Hydrochloric Acid → 1-(4-Methylcyclohexyl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

180 ml (0.36 mol) of a 2 M ethylmagnesium chloride solution in tetrahydrofuran (THF) was first treated with a solution of 37.8 g (0.3 mol) of 4-methylcyclohexanecarbaldehyde (cis/trans) in 70 ml of THF and then stirred under protective gas atmosphere for approximately 16 hours at 20-25° C. After addition of 250 ml of 15% by weight ammonium chloride solution, the mixture was acidified with semiconcentrated hydrochloric acid and then extracted with methyl tert-butyl ether (MTBE). Washing of the combined organic phases with water and drying gave 44 g of 1-(4-methylcyclohexyl)propan-1-ol as a colorless oil. According to 1H NMR analysis, the ratio between the cis and trans isomers in the mixture amounted to approximately 35:65.

Provenance & Evidence