Dimethyl Sulfoxide → Methyl 4-formylcyclohexane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Dimethyl sulphoxide (0.65 ml) in dry dichloromethane (5 ml) was added to a solution of oxalyl chloride (0.363 ml) in dichloromethane (5 ml) at -70° C. under a stream of nitrogen. After 5 minutes stirring a solution of methyl 4-hydroxymethylcyclohexanecarboxylate (0.64 g) in dichloromethane (5 ml) was added dropwise. The reaction mixture was stirred for 30 minutes at -70° C. Triethylamine (2.60 ml) was then added and the reaction mixture allowed to warm to room temperature during a period of 3 hours. After pouring into water (100 ml) the organic phase was washed with dilute hydrochloric acid, sodium bicarbonate solution and brine before drying over magnesium sulphate. Evaporation in vacuo gave methyl 4-formylcyclohexanecarboxylate (0.58 g) as a mixture of cis- and trans-isomers.

Provenance & Evidence