Resorcinol → 3-(4-Methylcyclohexyloxy)phenol

Participants

Reaction Steps

In a four necked flask (2 L) sufficiently dried, substituted with nitrogen, and equipped with a dropping funnel, Dimroth condenser tube, thermometer and stirring blade, resorcinol (110 g, 1.0 mol), 4-methylcyclohexanol (114 g, 1.0 mol) and triphenylphosphine (393 g, 1.5 mol) were dissolved in dried tetrahydrofuran (500 ml) under a nitrogen gas stream, and a mixed solution of diisopropyl azodicarboxylate (269 g, 1.3 mol) and dried tetrahydrofuran (400 ml) was dropped for 1 hour while cooling with iced saline solution. Next, it was stirred at room temperature for 12 hours. After the reaction terminated, 30% hydrogen peroxide (200 ml) was dropped through the dropping funnel for 10 minutes, then the reaction solution was dissolved in 2 L toluene, and washed three times with 1 L water. Toluene was distilled away by evaporation, and the residue was purified by column chromatography using hexane and ethyl acetate as developing solvents, to obtain a red brown objective product (hereinafter, referred to as R-2A) (45.0 g, 22% yield, 97% GC purity).

Provenance & Evidence