Hydrochloric Acid → Cyclopentanesulfonic acid

Participants

Reaction Conditions

Reaction Steps

A one liter three-neck flask was charged with 300 mL of methylene chloride and 25 grams (245 mmole) of cyclopentyl mercaptan to produce a reaction solution. The reaction solution was chilled to 15° C. in an ice-water bath and followed by the addition of 190 mL of 35% peroxy acetic acid. Said peroxy acetic acid was added over a period of about 3 hours and the reaction solution was maintained at a temperature of about 18°-26° C. After the reaction solution was stirred overnight at room temperature, 100 mL of water and 25 grams of sodium bisulfite were added followed by 2 additional hours of stirring. The reaction solution was then reduced on a rotovap and the pH was adjusted with dilute hydrochloric acid until a white solid precipitate formed. Said precipitate was isolated via filtration and dried in vacuo (50% yield of cyclopentane sulfonic acid).

Provenance & Evidence