Aluminium lithium hydride → 2,3,6-Trimethyl-4-sulfanylphenol

Participants

Reaction Conditions

Reaction Steps

A solution of 2,3,6-trimethyl-4-thiocyanato-phenol (45.7 g, 237 mmol) in anhydrous THF (300 mL) was added to a suspension of LiAlH4 (9.09 g) in anhydrous THF (600 mL) stirred at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 15 h. It was subsequently quenched with THF, followed by H2O and 0.5 M aq. HCl. Extraction with EtOAc (3×) was followed by washing the collected organic fractions with brine, drying over Na2SO4 and solvent evaporation. Column chromatography (SiO2: hexane:EtOAc, 9:1 v/v) yielded 4-mercapto-2,3,6-trimethyl-phenol as a white solid (32 g).

Provenance & Evidence