Molecular compounds of the following hydro

carbons and 2 mols. of picric acid, styphnic acid, or 1 : 3 : 5-trinitrobcnzene are described : aS-diphenyl- A“-butene (picrate, m. p. 102° with previous sintering;

trinitrobenzene, m. p. 101°); a£-diphenyl-Aaf-hexadiene (picrate, m. p. 112° with previous sintering; trinitro­

benzene, m. p. 145— 145-5°); ai-diphenylhexatriene

2 8 2 B R IT IS H CH EM ICA L ABSTRA CTS.— A .

(picrate, m. p. 170°; slyphnate, m. p. 193— 194°;

trinitrobenzene, m. p. 161— 162°); aS-di(diphenylene)- butadłene [picrate, m. p. 262° (decom p.); trinitro­

benzene, m. p. 240° (decomp.)]. The picrates of ai(-di(diphenyleno)hexatriene and a-phenyl-i-diphenyl- enehexatriene have m. p. 270° (decomp.) and 179°

(decomp.), respectively. The colours of solutions of a large number of the hydrocarbons in concentrated sulphuric acid, chloroform, and concentrated sulphuric acid, and acetic anhydride, chloroform, and concen­

trated sulphuric acid, and the position of the maximum bands of the absorption spectra are given.

H . Bu r t o n. N itr a tio n of a n th r a cen e to 9 : 9 '-d in itr o -9 : 9'- d ih y d r o x y -1 0 : lO '-d ih yd rod ian th racen e. J. S.

Tu r s k i and A. Be r l a n d s t e i n (Rocz. Chem., 1927, 7, 457— 466).— Anthracene yields on nitration under certain special conditions 9 : 9'-dinUro-9 : 9'-dihydroxy- 10 : 10'-dihydrodianthracene, m. p. 267— 268°, soluble in sodium hydroxide and yielding anthraquinone on oxidation. R . Tr u s z k o w s k i.

P e r y le n e and it s d eriv a tiv es. XVI. A. Zi n k e, K. Fu n k e, and H. Ip a v i c (Monatsh., 1927, 48, 741—

754; cf. A., 1926, 71; A., 1927, 350).—Chlorination of perylene in ice-cold carbon tetrachloride suspension affords a compound, C20H n Cl0, m ..p . 235° after pre­

vious darkening and sintering. Similar treatment of 3 ; 9-dichloro- or 3 : 9-dibromo-perylenes gives the compounds C20H 9C17 and C20H9Cl5Br2, m. p. 260°

(decomp.) and m. p. 240° (decomp.), respectively.

When perylene is chlorinated in nitrobenzene solution a t 130— 140° there is formed hexachloroperylene (A., 1925, i, 384), whilst in presence of anhjfdrous alumin­

ium chloride and nitrobenzene decachlorotetrahydro- perylene, m. p. above 400°, is produced. This com­

pound is converted by fuming sulphuric acid at 150—

160° into octachloro-octahydroperylene-3 : 4 : 9 : 10- diquinbne, m. p. above 400°, which when reduced with alkaline sodium hyposulphite and treated with the appropriate aroyl chloride affords the telrabenzoyl, m. p. 322-5° (decomp.), and letra-p-bromobenzoyl, m. p.

375° (decomp.), derivatives of tetracliloroperylene- 3 : 4 : 9 : 10-diquinol. The benzoyl derivative is hydrolysed and oxidised at the same tim e by warm concentrated sulphuric acid into tetrachloroperylene- 3 : 4 : 9 : 10-rit- quinone (annexed formula), also produced from the above octa- chloro-quinone by reduction with - 2 amalgamated zinc and hydro­

chloric-acetic acids.

Reduction of the octachloro-quinone w ith warm alkaline sodium hyposulphite followed by atmo­

spheric oxidation affords a green substance (prob­

ably a quinhydrone) which when treated w ith cold concentrated sulphuric acid yields a dark brown substance, C20H 5O4Cl5. Treatment of the octachloro- quinone with boiling aniline furnishes a compound, Ca8H250 4N 3Cl,, m. p. 305—307° (decomp.), whilst distillation with zinc dust and zinc chloride gives

perylene. H. Bu r t o n.

H y d ro g en a tio n of a n ilin e u n d er p r e s s u r e in th e p r esen ce of o s m iu m an d ir id iu m . W . S.

Sa d i k o v and A. L. Iv l e b a n s k y (Ber., 1928, 61, [£],

131— 137).—The osmium catalyst is prepared by reducing osmie acid on asbestos with hydrazine.

Hydrogenation is effected at 300° under high pres­

sure; tho extent of the reaction depends largely on the purity of the aniline and the mass of the catalyst.

An equilibrium appears to be established between catalyst, initial substance, and hydrogenated products.

In one instance the final material contained benzene 4%, cyclohexylamine 25%, dicyclohexylamine 20%, cyclohexylaniline 5%, and unchanged aniline 29%.

The iridium catalyst is formed by reduction of ammonium chloroiridate and activated by treatment with oxygen at 350— 400°. The observed products of hydrogenation of aniline are benzene, cyclohexane,

•q/clohexylamine, dicycZoliexylamine, and unchanged anilino. Hydrogenation occurs more readily in tho presence of osmium than of iridium and less decom­

position is observed. H. Wr e n. R ed u ction of n itr o -d e r iv a tiv e s w ith iro n and so lu b le ch lo rid es. A. Br e t n u t z and A. Pe n s a

(Notiz. chim.-ind., 1927, 2, 183; Chem. Zentr., 1927, ii, 243—244).—Iron filings, in presence of aqueous ferric chloride (preferably) or sodium chloride solu­

tion, stirred at 34 r.p.m. (opt.), was used as a reducing agent for nitrobenzene, p-nitrotoluene, m-dinitro- benzene to m-nitroaniline, p-nitrophenol, and picric acid. Nitrobenzene is readily reduced to aniline (1— 1-5 hrs. at 100°) when the chlorine concentration (ferric chloride) is 0-0174— 0-0319 g./c.c. p-Nitro- toluene (100 g.) gives a theoretical yield with 132 g.

of iron and 0-0259 g. of chlorine as ferric, chloride in 2 h rs.; m-dinitrobenzeno gives a theoretical yield of m-nitroaniline in 2-5 hrs. using 0-035 g. of chlorine per c.c. p-Nitrophenol (25 g.) is completely reduced in 1-25 hrs. on a boiling water-bath with 0-009 g. of chlorine per c.c. of solution. Picric acid is vigorously

reduced. A. A. El d r i d g e.

A n o m a lo u s effect of o -p -o rie n tin g g r o u p s on th e m . p. of d ih a lo g en a ted b en zen e d eriv a tiv es.

G. B. He i s i g (J. Amer. Chem. Soc., 192S, 50, 139—

145).— 2-Chloro-±-bromo-6-iodoaniline, m. p. 97— 97-5°, is obtained by treating 2-chloro-4-bromoaniline in aqueous acetic acid with iodine chloride. 4 -Ohloro- 2-bromo-6-iodoaniline, m. p. 109-5—110°, is obtained similarly from 4-chloro-2-bromoaniline. 2-Chloro-Q- bromoA-iodoaniline, m. p. 115-5— 116°, is obtained by brominating 2-chloro-4dodoaniline in glacial acetic acid, or by chlorinating 2-bromo-4-iodoaniline (acetyl derivative, m. p. 140— 140-5°). s-Chloro- bromoiodobenzene, m. p. 85-5—86°, is obtained from either of the above trihalogenated anilines by treat­

ment with sodium nitrite and sulphuric acid in boiling alcohol.

The m. p. of an o- or ?n-dihalogenobenzene is always raised by the introduction of a third substituent. The m. p. of a p-dihalogenobenzene is raised similarly if the entering substituent is one which causes m-substitu- tion, but 2 : 5-dibromo- and 2 : 5-di-iodo-nitrobenzene are exceptional, both having a lower m. p. than the corresponding dihalogeno-derivative. The m. p. of a p-dihalogenobenzene is generally lowered by the introduction of a third substituent having o-p-orient­

ing influence, but 2 : 5-dichlorophenol has a higher m. p. than p-dichlorobenzcne. F. G. Wi l l s o n.

ORGANIC CH EM ISTRY. 2 8 3

A cety len e d er iv a tiv e s. V II. R ea ctio n of tr i- ch loroeth ylen e w ith a m in e s. P. R u g g li and I.

Ma r s z a k (Helv. Chim. Acta, 1928, 11, 180— 196).— Phenylglycinediphenylamidine (Sabanejev’s base, A., 1876, i, 65), NHPh-CH2-C(:NPh)-NHPh (I), m. p.

190° (picrate, decorap. 135— 140°), is prepared from trichloroethylene (1 mol.), aniline (3 mols.), and 15%

aqueous sodium hydroxide (3 mols.) by heating for 40 hrs.; from phenylglycineanilide, aniline, and phosphorus trichloride a t 150°; from phenylglycine, aniline, and phosphorus trichloride at 160°, and from chloroacetic acid, aniline, and phosphorus trichloride at 160°. Benzoylation of the base yields N -benzoyl- plienylglycinedipliemjlamidinc, m. p. 142°, and bromin- ation in presence of chloroform and anhydrous sodium carbonate gives p-bromophenylglycine-p-bromb- anilide. When the base is treated with boiling alcohol for 60 hrs. or with aniline and aniline hydrochloride in boiling alcohol for 24 hrs. there is formed phenyl­

glycineanilide. Prom trichloroethylene and p-tolu- idine, p-anisidine, p-phenetidine, and 4-aminodi- phenyl there are formed p4olylglycinedi-p4olylamidine, m. p. 157°; p-amsylglycinedi-p-anisylamidine, m. p.

158— 159°; ■p-phenetylglycinedi-'p-irfienetylamidine, m. p. 112— 113°, and 4 • diplienylylglyc incdi-4-di­

phenyl ylamidine, m. p. 189— 190°. ■p-Anistylglycine- p -anisidide a.n&phenylglycine-p-bro7noanilide have m. p.

132° and 153— 154°, respectively. H. Bu r t o n. O dour and c o n stitu tio n a m o n g th e a r o m a tic m u sta rd o ils [th io ca rb im id es]. I. G. M. Dy s o n

(Perf. Ess. Oil Rec., 1928, 19, 3—5; cf. B., 1926, 215).—Tlio effect of alkyl substituents on the odour of aromatic thiocarbimides has been examined. In phenylthiocarbimide the introduction of an o-methyl group contributes sweetness, the »¡-group pungency, and the p-group an anise-like character. In the six xylyl thiocarbimides, duplication of a m ethyl group in the same orientation strengthens the effect. When both o- and m-methyl groups are present together the effect of the «¡.-group predominates and the 2 :3- and 2 : 5-xylylthiocarbimides are pungent. The influence of the p-groups overwhelms that of the o- or »¡-groups. Similar considerations apply in the 2 : 4 : 6-, 2 : 4 : 5-, and 2 : 3 : 5-trimethylphenvlthio- carbimidcs. Pentamcthylphenylthiocarbimide has only a very faint floral odour. p-Ethyl- and w-propyl- phenylthiocarbimides have a strong anise-like odour, whereas the corresponding 4-isopropylpbenylthiocarb- imide, b. p. 271°, has a harsher odour. 2-Cymyl- tMocarbimide, b. p. 268°, is distinctly pungent. The following compounds are described: o-3-xylylthio- carbimide, b. p. 262°, o-3-xylylthiocarbamide, m. p.

182 ; p-isopropylphmylthiocarbamide, m. p. 167°;

s-di-p-isopropylphenylthioca rbamide, m. p. 198°;

2-cymyltliiocarbamide, m. p. 174°; s-di-2-cymylthio- carbamide, m. p. 202°. E. H. Sh a r p l e s.

O rien tation effects in th e d ip h en yl se r ie s. V.

In d ep en d en ce of th e tw o n u clei in d ip h en yl c o m ­ pou n d s. R . J . W. Le F £v r e and E . E . Tu r n e r

(J.C.S., 1928, 245—255; cf. A., 1926, 946, 1029, 1131).-—The compound obtained by hydrolysis of the nitration product of phthalylbenzidine is mainly 2-nitrobenzidine (cf. Roller, A., 1904, i, 778). Nitr­

ation of 4-acetamidodiphenyl in acetic acid with

subsequent hydrolysis of the dinitro-derivative pro­

duced affords 3 : 4'-dinitro-4-aminodiphenyl, which is reduced by aqueous-alcoholic ammonium sulphide to 3-nitrobenzidine, m. p. 20S—210°. Nitration of the diacetyl derivative, m. p. 249—250°, of this com­

pound, followed by hydrolysis, yields 3 : 3'-dinitro- benzidinc. 4-67; loro A' -ph th a lim idodiphe/nyl, m. p.

245°, furnishes after nitration and hydrolysis 4-chloro-2 : 3'dinitro-4'-aminodiphenyl and 4-chloro-3 : 4-chloro-2'-di- nitro-4'-aminodiphcnyl, which is converted by alcoholic ammonia at 160— 180° into 2 : 3'-dinitro- benzidine. Similar results are obtained using 4 -bronw- 4'-phihalimidodiplienyl, m. p. 260°.

B y boiling benzidine with an excess of the appro­

priate ester the following derivatives were prepared : NW-di-o-carbetlwxybanzoyl-, m. p. above 300°; NN'- dicinnamoyl-, NN'-dicarbethoxy-benzidines, and 4 : 4'- diethyloxamidodiphenyl. Dinitration of those last two compounds with subsequent hydrolysis affords 3 : 3'-dinitrobcnzidine (Strakosch’s dinitrobenzidine, Ber., 1872, 5, 236). N N '-Diairbethoxy-derivatives were prepared from the following benzidines and ethyl chloroformate : 2-nitrobenzidine, m. p. 187—

188°; 2 : 2'-dinitrobenzidine, m. p. 200—201°; 2: 3 ' - dinitrobenzidine, m. p. 158°, and 3 : 3'-dinitrobenz- idine m. p. 216—217°.

Chlorination of 4-nitrodiphenyl in presence of a small amount of stannic iodide yields 4-chloro-4'- nitrodiphcnyl. The condensation product of benz­

idine with carbamide is NJV'-dicarbamylbenzidine (cf.

Schiff, A., 1878, 669; Michler and Zimmermann, A., 18S2, 182 ; Snape, A., 1896, i, 241). This compound can be used to detect traces of nitrates in concen­

trated sulphuric acid, a reddish-purple colour being produced at concentrations of 1 g. in 500,000 c.c.

The orientation experiments show that one nucleus in diphenyl, even if substituted (CcH 4R -), always exerts an op-directing influence. If the 4'-position is occupied by an op-directing group the radical CfiH4Rr- frequently exerts a small op-influence.

There appears to bo no mobile conjugation (electronic tautomerism) between the two nuclei, and it is con­

cluded that they are independent. Bell and Kenyon’s modification (A., 1927, 145) of Turner’s pnra-bridgo formula for diphenyl (A., 1923, i, 1085) is based on unsatisfactory evidence, and a slight modification (electronic) renders the formula satisfactory as a basis for explaining the laws of substitution in the diphenyl

series. H. Bu r t o n.

R ed u ctio n of a zob en zen e b y G rig n a rd r ea g e n ts.

H. Rh e i n b o l d t and R. Ki r b e r g (J. pr. Chem., 1928, [ii], 1 1 8 , 1— 13; cf. Franzen and Deibel, A., 1905, i, 843; Rheinboldt and Roleff, A., 1925, i, 542;

Gilman and Pickens, A., 1925, i, 1336; Gilman and Adams, A., 1926, 947).— Azobenzene reacts with 2 mols. of a Grignard reagent according to the equa­

tions : (i) N PhlN Ph+ 2RMgX=XMg'NPh-NPhMgX-f- 2R-; (ii) 2 R - = ( R - H ) + ( R + H ) ; (iff) 2R -= R ;R . If R = M e or Ph, (ii) does not occur, the product being ethane or diphenyl. When R = E t or Pra, (iii) is absent, and the products are ethylene and ethane, or propylene and propane. When R = • CH,,• CHMe2, (ii) and (iii) both occur, giving isobutylene (dibromide, b. p. 147— 149°), isobutane, and diisobutyl

[¡k-di-2 8 4 B R IT IS H CH EM ICA L A BSTRACTS.— A.

mcthylhexane], b. p. 10S— 110°. The formation of butane from azobenzene and magnesium ethyl bromide (Franzen and Deibel, loc. cit.) is not observed.

C . Ho l l i n s. C olour an d c o n stitu tio n . II. E ffec t of s u b ­ stitu e n ts on th e co lo u r of azo d y es. H . H . Ho d g s o n and F . W. Ha n d l e y (J.C.S., 1928, 162—

166).— Reduction of 3-chloro-6-nitrothioanisole with tin and acetic-hydrochloric acids furnishes 4-chloro- 2-thioanisidim (acetyl, m. p. 110°, and benzoyl, m. p.

106°, derivatives), whilst treatment with sodium disulphide yields 4 : 4'-dinitro-o : 5'-dimelhylthioldi-

■phenyl disulphide, m. p. 216— 217°. Treatment of this compound with hot alkaline sodium sulphide and subsequent addition of m ethyl sulphate gives 2 : 4-dimethylthiolnitrobenzcne, which furnishes 2 : 4- dimclhylthiolanilinc (hydrochloride, acetyl, m. p. 114°, and benzoyl, m. p. 125°, derivatives). 3-Chloro-6- nitroacctanilide and sodium disulphide yield 3 : 3'- d iacetamido-4 : 4'-dinitrodiphenyl disulphide, m. p.

192— 193°, which furnishes G-nitro-3-thioariisidine, m. p. 116°. Z-Chloro-4-niirothioanisole has m . p.

61° and yields 2-cldoroA-thioanisidine (hydrochloride, m. p. 217— 218°; acetyl derivative, m. p. 129°).

With |3-naphthol-6-mono- and -3 : 6-di-sulphonic acids as second components, azo dyes have been pre­

pared from the above thioanisidines, and from o-, m-, and p-cliloro-, 2 : 4- and 2 : 5-dichloro-, and 2 : 4-di- methoxy-anilines, 5-chloro-2-anisidine, 5-chloro-2-thio- anisidine, and aniline. The batliochromic effects of the different groups in different positions are tho same as those already described (A., 1926, 515).

H . Bu r t o n. P r e p a r a tio n of c y clo h ex a n o l e th e r s. F o r m ­ a tio n of te tra b en zy lc y cio h ex a n o n es. R . Co r n u- b e r t and H. L e Bi h a n (Bull. Soc. chim., 1928, [iv], 43, 74— 78).—The sodium compounds of cyclo- hexanols are readily obtained by the action of sod- amide in dilute ethereal solution (cf. A., 1927, 666);

with alkyl halides they afford the corresponding ethers.

Thus cydohcxanol with sodamide and m ethyl sulphate gives cyclohexyl m ethyl ether, b. p. 134-5— 135°, du-’ 0-8860, m“ 5 1-4390. 4-Mcthy cyclohexanol similarly yields 4-methylcyclohcxyl methyl ether, b. p.

151°, d»* 0-8612, nf,y 1-4321. Commercial “ p u r e ” cyclohexanol with allyl chloride or bromide affords cyclohexyl allyl ether, b. p. 83— S4°/38 mm., and a small quantity of a substance, C15H ,„0, b. p. 155—

158°/18 mm., probably a triallylcyclohexanone.

2-Methyl cyclohexyl methyl ether has b. p. 69—70°/15 mm. W ith benzyl chloride commercial cyclohexanol gives, in addition to cyclohexyl benzyl ether, b. p.

165-5— 166-5°, <f° 0-9941, 1-5178, a little tetra-benzylcyclohexanone, m. p. 178°, b. p. above 360°/

15 mm. 4-Methylcyclohexanol similarly affords 4-methylcjclohexyl benzyl ether, b. p. 153-5— 154°/17 mm., cP 0-96S1, nJJ 1-5090, and a little tetrabenzyl-4- melhylcyclohexanone, m. p. 1S4°. R . Br i g h t m a n.

P r e p a r a tio n of 2 -b r o m o -p -c r e so l fr o m p -n itr o - to lu en e. H . J. Lu c a s and N . F. Sc u d d e r (J. Amer.

Chem. Soc., 192S, 50, 244— 249).—2-Bromo-4-nitro- toluene is obtained in 76% yield by adding bromine in slight excess to p-nitrotolucne in presence of iron filings, with cooling. After keeping for 24 his., the

mixture is heated gradually to 150° until evolution of hydrogen bromide ceases (cf. Cohen and Dutfc, J.C.S., 1914, 105, 505). Reduction of tho bromo- nitrotoluene with alcoholic ammonium sulphide affords 2-bromo-p-toluidine, m . p. 27-3—27-5°, in 84% yield, and from this 2-bromo-p-cresol (benzoate, m. p. 74-6—75-1°) is obtained in 80-5% yield by adding a solution of tho diazotised amine gradually to a solution of sulphuric acid and sodium sulphate at 130— 140°, the cresol being distilled off as it is formed by a current of steam at 160— 180°.

F . 6 . Wi l l s o n. P re p a r a tio n of io d in e -su b stitu te d b en zo - n itr ile s of th e p h en o l eth er ty p e. Ch e m. Fa b r. a u f Ac t i e n (v o r m. E. Sc h e r i n g).—See B ., 1928, 83.

B a s e s o b ta in ed fr o m p -p h e n e tid in e and fr o m p -to lu id in e w ith fo rm a ld e h y d e in a cid s o lu tio n . R. Le p e t i t, G. Ma f f e i, and C. Ma i m e r i (Gazzetta, 1927, 57, 862— 871).— In addition to the products, already described (A., 1917, i, 452), the action of formaldehyde on p-phenetidino hydrochlorido at 60°

yields : (1) tho base, m. p. 132°, obtained by Reverdin (A., 1921, i, ,564) by treating methylenedi-p-phenet- idine with nitric a c id ; tho authors consider tho formula of this base to be, not G18H 240 2N 2 or Ci8H 220 2H2, but C19H 220 2N 2, which is in good agree­

ment with the results of Reverdin’s analyses of tho base, its nitrate , and nitroso-derivative; (2) a base, C 19Hm0 3N 2, m. p. 114°, the salts of which have a bitter taste and'anaesthetic properties.

Tho base, m. p. 140° (loc. cit.), gives the following derivatives: diacetyl, C21H 280 4N 2, m - P- —H 7°;

tw o benzoyl derivatives, C31H 2t)0 4N 2 (m. p. 180— 181°) and C2GH 280 4N 2 (m. p. 132— 133°); methyl derivative, m. p. 114°, identical with the base (2) (see above);

ethyl derivative, m. p. 82— 83°, and tho hydrochloride of the allyl derivative, C21H 270 3N 2C1, m. p. 202°.

When oxidised by means of acid permanganate, the base, m. p. 140°, yields a compound, in. p. 210°, of indifferent character; when reduced by zinc dust and acetic acid, it gives p-phenetidine, methyl-p- phenetidine, and a base, C29H 180 4N 2, m. p. 91°.

The interaction of p-toluidine and formaldehyde in acid solution yields : (1) a base, C17H 30ON2, m. p.

140°, probably identical with that of, m. p. 146—

147° obtained from p-phenetidine (loc. cit.); (2) a base, C16H 1KN 2, m. p. 158°; (3) m ethyl-p-toluidine;

(4) a base, OlTH 20ON2, m. p. 97— 98°, which forms an oxalate, Cl7I 1 18N 2,iI2C20 4, m. p. 255— 259° (de­

comp.); (5) a base, C17H 18N 2, m. p. 137— 138°.

T. H. Po p e. A d jacen t su b stitu tio n . I. R e a c tio n s of 3- c lilo r o -2 -a m in o a n iso le . H . H . Ho d g s o n and A.

Ke r s h a w (J.C.S., 1928, 191— 193).—Reduction of 3-chloro-2-nitroanisolc with iron powder and 50%

acetic acid gives 3-chloro-2-aminoanisole, b. p. 246°

(slight decomp.) (hydrochloride, m. p. 211°; hydro­

bromide, sublimes at 250°; nitrate, m. p. 137° ; acetyl, m. p. 123°, diacetyl, m. p. 145-5°, and benzoyl, m. p.

135°, derivatives). The sulphate is very soluble in water. B y the usual methods 2 : 3-dichloro-, m. p.

33° (cf. Hollemann, A., 1917, i, 556), 3-chloro-2- brmno-, m. p. 50°, H-chloro-2-iodo-, m. p. 53-5°, and

‘¿-chloro-2-cyano-anisoles, m. p. 114-5°, were prepared.

ORGANIC CHEM ISTRY . 2 8 5

‘¿-Chloro-'2-t1tiocyanoanisole lias in. p. 43°. Diazoiis- ation of the aminoanisolo yields stable diazoniuxu salts ivhich are unaffected by dilute acids, but the sulphate when treated w ith bromine gives 3-chloro- anisole-2-diazoperbromide, m. p. 115— 116° (decomp.).

This compound when boiled with acetic acid furnishes d-chloro-2 : G-dibromoanisolc, m. p. 92°, and with ammonia yields ‘¿-chloroanisolc-2-diazoimide, m. p. 35°.

Reduction of 3-chloroanisole-2-diazonium chloride.

affords 3-chloroanisyl-2-hydra,zim hydrochloride, and