Potassium Hydroxide → 5-(4-Hydroxyphenyl)-2-benzofurancarboxylic acid

Participants

Reaction Steps

A mixture of 10.4 g of 11 and 7.2 g of potassium hydroxide in 170 ml of ethanol was refluxed for 2 hours. The solvent was evaporated under reduced pressure. The residue was mixed with 200 ml of water, and the mixture was acidified to pH=2 with concentrated hydrochloric acid, stirred for 30 minutes and filtered. The solid was washed with water, dried under reduced pressure and mixed with tetrahydrofuran. The mixture was refluxed and filtered. The filtrate was concentrated, the residue was washed with ether and mixed with tetrahydrofuran. The mixture was filtered, the filtrate was concentrated to about one-fourth its volume and triturated with ether. The resulting solid was collected and dried under reduced pressure to give 16, mp: 297°-300° C.

Provenance & Evidence