— 145 — 



distillation of the two chlorides, when treated with alcoholic potash 

 liquor, gave a mixture of monochloride and a hydrocarbon (b. p. 177 

 to 185 ; do,845; n D 1,4718; «d±o°; MR.45,15), which yielded no 

 nitrosite, but a crystalline bromine compound. Kondakow and 

 Schindelmeiser therefore believe it to be dipentene. 



In their opinion the formation of pinene hydrochloride can be 

 attributed to the presence of pinene in the oil of water fennel, or to 

 a conversion of the phellandrene. Although the presence of pinene 

 in oil of water fennel has not yet been proved, various circumstances 

 indicated more in detail by the authors, allow of such a conclusion 

 being drawn. If- it should not be found possible to detect pinene in 

 oil of water fennel, the formation of pinene hydrochloride would probably 

 be due to a conversion of the phellandrene. In a theoretical study 

 on the constitution of the chlorides obtained, such a possibility is 

 discussed more in detail. 



Carvestrene. W. H. Perkin jun. and G. Tattersall 1 ) publish 

 a preliminary communication on the synthesis of carvestrene. If 

 m-hydroxybenzoic acid is reduced with sodium and alcohol, hexahydro- 

 m-hydroxybenzoic acid is formed, which is oxidised by bichromate and 

 sulphuric acid to y-ketohexahydrobenzoic acid (b. p. 210 [25 mm. 

 pressure]; m. p. 75 to 76 ). This yields a semicarbazone melting at 182 

 to 183 with decomposition. The ethyl ester of y-ketohexahydrobenzoic 

 acid, when treated with magnesium methyl iodide, is converted in the lac- 

 tone of y-hydroxyhexahydro-m-toluic acid (b. p. 145 [20 mm. pressure]). 

 When the latter is heated with hydrobromic acid, it yields ^-bromo- 

 hexahydro-m-toluic acid, which is converted by treatment with pyridine 

 in tetrahydro - m-toluic acid (b. p. 142 to 144 [15 mm. pressure]). 

 If magnesium methyl iodide is allowed to act on the ester of this acid, 

 there is formed J 1 -m-menthenol-8 (b. p. 1 ioto 1 12 [30 mm. pressure]), 

 and this yields, when heated with potassium bisulphate, with loss of 

 water, carvestrene (b. p. 179 to 180 ), which was identified by the 

 dihydrochloride (m. p. 52,5°) and the dihydrobromide (m. p. 48 ). 





Alcohols. 



For the production of glycols, the materials employed are frequently 

 either the corresponding bromides or unsaturated alcohols, or occasionally 

 also diamines, chlorohydrins, etc. The trouble, costliness, and comparat- 

 ively small yield of these methods have induced F. W. Semmler 2 ) 

 to look for a more rational method for the production of the glycols 

 of terpene derivatives, and he succeeded in producing y-, d~ and ^-glycols 



*) Proceed, chem. Soc. 22 (1906), 268. 

 2 ) Berl. Berichte 39 (1906), 2851. 



