Hexane → p-[4-(Methoxymethylene)cyclohexyl]benzonitrile

Participants

Reaction Steps

A suspension of 10.4 g of triphenyl-methoxymethyl-phosphonium chloride in 60 ml of t-butyl methyl ether was placed at -10° C. under argon gasification and treated within 10 minutes with 3.6 g of solid potassium t-butylate. After completion of the addition the reaction mixture was stirred at -10° C. to 0° C. for another 30 minutes and then treated dropwise at 0° C. with a solution of 4.2 g of 4-(p-cyanophenyl)cyclohexanone in 50 ml of absolute tetrahydrofuran. The reaction mixture was subsequently stirred at room temperature for another 2 hours, then poured into 500 ml of hexane and filtered. Low-pressure chromatography (0.5 bar) of the concentrated residue (7.1 g) on silica gel with ethyl acetate/petroleum ether (vol. 1:19) gave 4.5 g (94%) of p-[4-(methoxymethylene)cyclohexyl]benzonitrile as a colourless, gradually crystallizing oil (purity 95%); Rf-value (ethyl acetate/petroleum ether vol. 1:9)=0.30.

Provenance & Evidence