3,5-Di-tert-butyl-4-hydroxybenzoic acid → 3,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Participants

Reaction Conditions

Reaction Steps

To a 3-necked flask equipped with a magnetic stirrer, thermometer, and water condenser with a drying tube is added 3,5-di-t-butyl-4-hydroxybenzoic acid (12.5 g, 0.05 m), thionyl chloride (10 ml) and 5 drops of pyridine. This mixture is heated at 45° C. for 1.5 hr. After cooling to RT, 50 ml of benzene is added. After stirring for 15 min., the benzene is evaporated under water aspirator vacuum leaving a yellow solid. This is dissolved in petroleum ether (at 35°-55° C.), filtered, and evaporated to afford 11 g of a yellow solid, mp 90°-93° (lit.mp. 96°-99°).

Provenance & Evidence