Methyl vinyl ketone → HCID 14175218, compound

Participants

Reaction Steps

A solution of 2.7 g of 4-cyano-3-fluorophenol and 5 ml of pyridine in 30 ml of toluene is added dropwise to a solution of 6.1 g of p-(4-methyl-4-n-pentylcyclohexyl)benzoyl chloride [obtainable by reaction of the enamine, obtainable from 2-methylheptanal and pyrrolidine, with methyl vinyl ketone according to G. Otani and S. Yamada, Chem. Pharm. Bull. 21(10), 2112-2118 (1973), hydrogenation of the resulting 4-methyl-4-pentyl-2-cyclohexanone to give 4-methyl-4-pentylcyclohexanone (an intermediate of the formula (A)), reaction With phenyl magnesium bromide, hydrolysis and hydrogenation to 4-methyl-4-n-pentylcyclohexylbenzene, reaction with acetyl chloride in the presence of aluminium chloride, subsequent haloform degradation of the resulting acetophenone to give the corresponding benzoic acid and conversion to the acid chloride] in 40 ml of toluene, and the mixture is boiled for 2 hours. After the customary working-up, 4-cyano-3-fluorophenyl p-(4-methyl-4-n-pentylcyclohexyl)benzoate is obtained.

Provenance & Evidence