Acetic Acid → Benzenenonanoic acid, 4-hydroxy-

Participants

Reaction Steps

A mixture of 55.7 gms 9(4-methoxyphenyl)nonanoic acid, 640 ml 48% HBr and 640 ml acetic acid was refluxed for 7 hours and cooled to room temperature overnight. The solution was diluted with a large excess of water, whereupon a solid precipitated. The solid was filtered off, re-suspended in water, and filtered again. It was dissolved in ether, washed four times with water, and the organic phase was dried over MgSO4 overnight. The drying agent was filtered off and the solvent removed in vacuo to give a solid which was recrystallized from toluene to give 31.8 gms (58%) 9(4-hydroxyphenyl)nonanoic acid, m.p. 103°-5°.

Provenance & Evidence