Hexane → p-[2-(4-Methoxymethylenecyclohexyl)ethyl]benzonitrile

Participants

Reaction Conditions

Reaction Steps

A suspension of 54.4 g of methoxymethyl-triphenylphosphonium chloride in 315 ml of t-butyl methyl ether was treated with 18.8 g of potassium t-butylate while gassing with argon at -10° C. and the orange suspension was stirred for a further 30 minutes at 0° C. The mixture was subsequently treated dropwise within 30 minutes at 0° C. with a solution of 25.1 g of 4-[2-(p-cyanophenyl)ethyl]cyclohexanone in 260 ml of tetrahydrofuran and the mixture was stirred for a further 3 hours at room temperature. Thereafter, the reaction mixture was poured into 2.6 l of hexane, stirred for 10 minutes and suction filtered (rinsing with hexane). The filtrate was concentrated in vacuo at 50° C., whereby 47.7 g of yellow, partially crystalline residue were obtained. Low-pressure chromatography (0.3 bar) of the residue on silica gel with hexane/methylene chloride (vol. 4:1) and methylene chloride gave 21.0 g of p-[2-(4-methoxymethylenecyclohexyl)ethyl]benzonitrile as a yellowish oil; Rf-value (methylene chloride) 0.43.

Provenance & Evidence