Acetic Acid → 2-(3-Bromobutyl)-3-methyl-6-nitrophenol

Participants

Reaction Conditions

Reaction Steps

A mixture of 155 ml of the crude 1B, 15 ml of glacial acetic acid and 135 ml of 48% hydrobromic acid was stirred at reflux (113° C.) for five hours, then concentrated at 30 Torr. and 80° C. for one hour. The residue was taken up in 500 ml of ether, dried (MgSO4), and filtered through Celite, and the solvent was evaporated from the filtrate. The residue was column-chromatographed on silica gel, using a 1:24 v:v mixture of THF and hexane as eluent. The product was recrystallized from ether/hexane to give 2-(3-bromobutyl)-3-methyl-6-nitrophenol (1C), as a light yellow solid, m.p.: 67°-69° C.

Provenance & Evidence