Hydrochloric Acid → Tetrahydrothiopyran-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of tetrahydro-thiopyran-4-carbonitrile (646 mmol), in ethanol (600 ml) was added in one portion to a rapidly stirring mixture of sodium hydroxide (258.4 g, 6.46 mol) in water (1.1 L). The mixture was then heated to 90° C. for 2 h, cooled to 0° C. and the pH adjusted to 2 with conc. hydrochloric acid solution. The ethanol was then removed in vacuo and the suspension extracted into dichloromethane (3×1 L). The combined organic extracts were then dried over magnesium sulfate and evaporated in vacuo to give tetrahydro-thiopyran-4-carboxylic acid as a brown solid (96 g, 646 mmol).

Provenance & Evidence