Molbank 2003, M318 www.molbank.org (±)-1-(4-Hydroxy-3-methoxyphenyl)-4-methyl-3-pentanol

The discussion and purpose for the synthesis of this compound has been reported elsewhere [1]. To a cold (0°C) solution of 1-(4-hydroxy-3-methoxyphenyl)-4-methyl-3-pentanone (190 mg, 0.86 mmol) in EtOH (15 mL) was added sodium borohydride (40 mg, 1.1 mmol, 1.3 eq). The solution was stirred at 0°C for 30 min., then at room temperature for 1 h. 10 % HCl (10 mL) was added and the solution was stirred at room temperature for 2 h. The solution was concentrated in vacuo and the aqueous residue was extracted with dichloromethane (3 x 10 mL). The organic fractions were combined, dried (MgSO4) and the solvent was evaporated in vacuo. Chromatography on silica gel (40 % EtOAc / hexanes) afforded a white solid (172 mg, 90%). mp: 55-56°C. IR (KBr) cm-1: 3397 (OH)