156 Report of Schimmel § Co. April/October 1917. 



Methylenecamphor acetic acid reacts in an alkaline solution with diazonium salts, 

 producing strongly-coloured formazyl derivatives; the result of its combination with 

 diazobenzene sulphonic acid is a good dye for wool. 



Under the influence of concentrated sulphuric acid, methylenecamphor acetic acid 

 is converted into a new compound, namely a ^-lactone melting at 66°. 



Methylenecamphor acetic acid is easily deprived of its carboxyl group, thereby forming 

 ethylidene-3-camphor (methylmethylene camphor), when heated with water under pressure. 



The reaction between methylbensoate and phenylmagnesiumbromide. — G. Stadnikow 1 ), in 

 continuing his investigations on the effects of esters on organic magnesium compounds 2 ), 

 has studied the reaction of methylbenzoate on phenylmagnesiumbromide in an ethereal 

 solution free of water, whereby he found that triphenylmethylether and triphenylcarbinol 

 were formed. On allowing benzylbenzoate to act on phenylmagnesiumbromide, dissolved 

 in boiling ether, triphenylmethylbenzylether and triphenylcarbinole resulted. If the process 

 is conducted at a temperature of 100°, one obtains a yield of 15 per cent, triphenyl- 

 carbinol and 30 per cent, of triphenylmethylbenzylether. The product of the reaction 

 contains benzylbromide besides. The combination of ethylacetate and of phenylmagnesium- 

 bromide at the boiling point of ether yields a-diphenyl ethylene. When an ethereal solution 

 of phenylmagnesiumbromide is brought in contact with benzylacetate at a low temperature, 

 the results are methyldiphenylcarbinol arid benzylalcohol. The same reaction conducted 

 at the boiling point of ether produces, besides the two above-mentioned compounds, 

 diphenylethylene. 



Nitrogenous compounds. 



Reduction of azothymol and of azocarvacrol. — While investigating the reducing qualities 

 of phenylhydrazine, E. Puxeddu 3 ) also studied the reduction of some diazo compounds. 

 Under these circumstances he found that monoazothymol (benzene-azo-thymol), a sub- 

 stance melting at 112 to 114°, which is the result of the reaction of thymol and of 

 benzenediazoniumchloride, besides the formation of the diazo-compound, produces, when 

 heated with phenylhydrazine, aminothymol (II), melting at 178 to 179°, which latter reacts 

 with ferric chloride, producing thymoquinone. ZtazOthymol fcfo'sbenzeneazothymol) (I), 



N:NC 6 H 5 NH 2 NH 2 CH 3 OH 



H 3 C 



C 6 H 6 N:N 



H,C / > H 3 C 



C3 H7 k. ) C3 H7 H 2 N 



C3 H7 H2 IS 



OH 



CHO 



OH OH OH C 3 H 7 N:NC 6 H 6 



(I) Disazothymol (II) Aminothymol. (Ill) Diaminothymol. (IV) Aminocarvacrol. (V) Benzeneazo- 



(Disbenzeneazothymol). salicylic aldehyde. 



a by-product of the preparation of monoazothymol, melts at 180 to 185°, and yields, 

 on being reduced with phenylhydrazine, apparently diaminothymol (III) which, however, 

 is decomposed at 255°, becoming brown at the same time, and is converted, on treatment 

 with ferric chloride, into a hydroxythymoquinone. Monoazaocarvacrol (benzeneazo- 

 carvacrol) originates from carvacrol and benzenediazonium chloride at the same time 

 as the diazo compound; it melts at 85° and produces, on being reduced by phenyl- 



i) Journ. russ.phys. chem. Ges. 47 (1916), 2037, 2115; Chem. Zentralbl. 1916, II. 388. — 2 ) Comp. Eepor 

 October 1916, 118. — ») Gazz. chim. ital. 46 (1916), I. 62, 211; Chem. Zentralbl. 1916, I. 883; II. 471. 



