Dimethyl Sulfoxide → HCID 178509751, compound

Participants

Reaction Steps

A mixture of 9.3 g of oxalyl chloride and 166 ml of methylene chloride was treated dropwise with 10 minutes with a solution of 11.4 g of dimethyl sulphoxide in 33 ml of methylene chloride while stirring and gassing with nitrogen at -60° C. Thereafter, the mixture was treated dropwise within 15 minutes at -60° C. with a solution of 16.2 g of p-[2-(trans-4-hydroxymethylcyclohexyl)ethyl]benzonitrile in 66 ml of methylene chloride and the resulting mixture was stirred for a further 15 minutes at -60° C. Subsequently, the reaction mixture was treated dropwise within 15 minutes at -60° C. with 46.6 ml of triethylamine, the mixture was then warmed to room temperature within 30 minutes, poured into 330 ml of water and extracted three times with 200 ml of methylene chloride each time. The organic phases were washed twice with 200 ml of water each time, dried over sodium sulphate and concentrated at 50° C. in vacuo. Low-pressure chromatography (0.3 bar) of the resulting, brownish crystals (16.5 g) on silica gel with methylene chloride gave 14.4 g (89.6%) of pure trans-4-[2-(p-cyanophenyl)ethyl]cyclohexanecarboxaldehyde as colourless crystals with m.p. 90.0°-91.2° C.

Provenance & Evidence