Hydrochloric Acid → (4-Chlorophenyl)(5-ethyl-2-hydroxyphenyl)methanone

Participants

Reaction Conditions

Reaction Steps

Aluminum chloride (267g) was added in portions over 30 minutes to a stirred solution of 4-ethylphenol (122.1g.) and 4-chloro-benzoyl chloride (140ml.) in dry 1,1,2,2-tetrachloroethane (800ml.). The mixture was heated at 105°C. for 22 hours with stirring, and on cooling a mixture of ice (600g) and concentrated hydrochloric acid was added slowly, A vigorous reaction occurred and some material was lost. The remaining material was separated and the aqueous fraction extracted twice with chloroform (200ml.), and the combined organic layers evaporated to a dark oil which was distilled in vacuo giving two main fractions: B (17.4g) 150°-160°C at 0.3mmHg; C (110.8g) 160°-168°C at 0.3mmHg. Both remained liquid on cooling.

Provenance & Evidence