Triethylamine → Phenylacetic Acid

Participants

Reaction Steps

A mixture of 8.3 g of 2-tosyltropone, 4.5 g of p-aminophenylacetic acid and 9 ml of triethylamine in 200 ml of tert-butylalcohol was refluxed for 24 hours. The mixture was concentrated and acidified with 2 N hydrochloric acid, followed by extraction with dichloromethane. The dichloromethane solution was extracted with a saturated sodium bicarbonate aqueous solution. The aqueous layer was acidified and extracted with dichloromethane. The dichloromethane solution was washed with water and dried over anhydrous magnesium sulfate and evaporated to give a yellow crystalline solid, which was recrystallized from ethanol to yield 4.6 g of p-(2-troponylamino) phenylacetic acid; m.p. 175°-176° C.; Analysis--Calculated for C15H13NO3 : C 70.58%, H 5.13%, N 5.49%; Found: C70.34%, H 5.30%, N 5.55%.

Provenance & Evidence