Hydrochloric Acid → 4,4-Dimethylcyclohexanecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

2-(4,4-Dimethyl-cyclohexylidene)-[1,3]dithiane (21.6 g, 95 mmol) and TFA (30.5 mL, 0.32 mol) were placed in acetonitrile (100 mL) and water (25 mL) and the mixture was heated at 65° C. for 3 h. 30% Aqueous hydrogen peroxide (152 mL, 1.3 mol) was added carefully and the mixture was warmed to 80° C. slowly. After 1 h, the reaction mixture was cooled to 40° C. and was added slowly to an aqueous solution of NaOH (6N, 630 mL). The resulting mixture was cooled to 0° C. and acidified with aqueous 6N HCl. Dichloromethane (500 mL) was added and the mixture was filtered. The aqueous phase was extracted with dichloromethane (100 mL×5), was dried (MgSO4) and was evaporated in vacuo to yield the title compound (12 g, 81%). MH+157.

Provenance & Evidence