Hydroquinone → (-)-p-(2-Cyano-2-methylhexyloxy)phenol

Participants

Reaction Conditions

Reaction Steps

While 480 mg (1.6 mM) of (+) 2-cyano-2-methylhexyl p-toluenesulfonate, 357 mg (3.2 mM) of hydroquinone and 1.5 ml of n-butanol were stirred in a nitrogen atmosphere, sodium butoxide obtained by dissolving 83.3 mM (2.1 mM) of sodium hydroxide in 2.2 ml of n-butanol was added dropwise, followed by stirring for 20 hours under heating at 120° C. After the reaction, 5 ml of saturated sodium chloride aqueous solution was added, followed by extraction with ether. The ether layer was washed with distilled water and dried on sodium sulfate, followed by distilling-off of the solvent to obtain 296 mg of a crude product, which was then purified by thine layer chromatography (developer solvent: methylene chloride) to obtain 81.3 mg of (-)-p-(2-cyano-2-methylhexyloxy)phenol (Yield: 19.1%). [α]D -1.8 degree (c 0.836, benzene).

Provenance & Evidence