3-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)propionic acid → HCID 13135952, compound

Participants

Reaction Steps

A mixture of 23.4 g. (0.1 mole) ethyl 4-(piperazin-1-yl)-benzoate (base), 600 ml. xylene and 27.8 g. (0.1 mole) 3-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionic acid is boiled under a water separator for 28 hours, then evaporated to dryness in a vacuum and the residue is taken up with diethyl ether. For the removal of unreacted ethyl 4-(piperazin-1-yl)-benzoate, the ether solution is extracted with 1N hydrochloric acid, washed with water and aqueous sodium bicarbonate solution, dried with anhydrous sodium sulphate and mixed with hydrogen chloride-containing diethyl ether, whereby the hydrochloride precipitates out. This is washed with diethyl ether and recrystallised from ethanol to give 32.0 g. (60% of theory) of the desired product as colourless crystals; m.p. 196°-198° C.

Provenance & Evidence