- 186 — 



Some years ago we described Bcedtker's 1 ) experiments in the action . 

 of Grignard's salts upon ethyl- and benzal-menthone, and in our notice 

 we referred among other bodies to menthodiphenylmethane, which occurs 

 in the form of three isomerides. Boedtker 2 ) has now oxidised with chromic 

 acid in a glacial acetic acid solution the modifications of menthodiphenyl 

 methane which melt at 140° and between 136 and 137° respectively, and 

 has obtained benzophenone, which proves that the two phenyl groups are 

 found at the same carbon atom. 



Boedtker prepared menthomethylphenylmethane by condensing benzyl- 

 idene menthone with magnesiummethyl iodide: m. p. Ill to 112°; [a] D19 o 

 + 95° 16' (in benzene), of which the benzoate melts at 152 to 153°. 

 He also describes menthyHsoamyl phenylmethane: b. p. 215° (15 mm.), 

 Md20,5o + 13°45' (in benzene solution), which yields a benzoate melting 

 between 93 and 94°. 



In conclusion Boedtker mentions benzoylmenthone, a liquid with 

 b. p. 185° (12 mm.) ([a] D20 ,5o + 30° 11' in benzene solution, n D2 i, 8 o 1,51745). 



By condensing natural menthone (b. p. 208 to 209°; d o 0,8941 ; 

 Wd — 23,6°) with magnesium phenyl bromide, M. Murat 3 ) has prepared 

 the tertiary alcohol methyl- l-phenyl-3-isopropyl-4-c^cfohexanol-3: b. p. 175° 

 (20 mm.), d o 0,9962, d 20 o 0,9843, n D 1,527. No phenylurethane was obtained. 

 Treatment of the alcohol with water-eliminating agents (the readiest method 

 being by passing it over aluminium at 300°) gives rise to m ethyl- 1-pheny 1-3- 

 isopropyl-4-cycZohexerie (b. p. 268 to 272°; d o 0,9700; d 20 o 0,9621 ; n D 1,537). 



When treated with magnesium cyclohexyl chloride menthone yields 

 methyl-l-c^dohexyl-3-^opropyl-4-c^cZohexanol-3 (q/dohexylmenthol) (m. p. 

 92°), from which, by splitting off water, methyl-l-c^cfohexyl-3-isopropyl-4- 

 q/cfohexene, results. This hydrocarbon has an odour of garlic and 

 possesses the following constants: b. p. 265°, [«] D + 6,2°, d o 0,9897, 

 d 14 o 0,9198, n D 1,498. 



Murat has also carried out the reaction of thymomenthone with 

 magnesium phenyl bromide. This ketone, which has b. p. 212°, he pre- 

 pared by passing thymomenthol over copper heated to 300°. i-Phenyl- 

 thymomenthol possesses the following constants: b. p. 170° (18 mm.), 

 d o 0,9950, n D180 1,526. The corresponding menthene boils between 270 

 and 272°. 



The boiling point of i-q/cfohexylthymomenthol, a body which results from 

 the condensation of thymomenthone with cyclohexyl magnesium bromide, if 

 about 164° (15 mm., with partial decomposition): d o 0,9931 , n^o 1,529. 

 This body yields a q/cZohexylthymomenthene with b. p. 260° (756 mm.). 



!) Compt. rend. 145 (1907), 392; Report October 1907, 160. 



2 ) Compt. rend. 154 (1912), 437. 



3 ) journ. de Pharm. et Chim. 103 (1911), 294. 



