Hydrochloric Acid → DH 990

Participants

Reaction Steps

The ethyl 2-((3,5-di-tert-butyl-4-hydroxyphenyl)thio)hexanoate product (75 grams; 0.195 mole) obtained in Example 2 was dispersed in 300 ml. of 95% ethanol and 500 ml. of 5N potassium hydroxide added thereto. The resulting reaction mixture was heated on a steam bath at the boiling point under gentle reflux for about 90 minutes with occasional stirring. Following the heating period, the reaction mixture was poured into 2000 ml. of 5% HCl with vigorous stirring. The white precipitate formed upon acidification was obtained by filtration and washed with water. Recrystallization (twice) of the precipitate from a methylene chloride-hexane mixture gave the desired 2-((3,5-di-tert-butyl-4-hydroxyphenyl)thio)hexanoic acid compound having a melting point of 140°-142° C.

Provenance & Evidence