Water → [3-Methoxy-5-(3-methoxypropoxy)phenyl]methanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-Methoxy-5-(3-methoxy-propoxy)-benzoic acid methyl ester (5 g, 19.7 mmol) and LAH (528 mg, 20 mmol) in THF (110 mL) is stirred under N2 at 0° C. for 3 h. After adding H2O, the reaction mixture is extracted with EtOAc. The combined organic phases are washed with H2O, brine and dried (Na2SO4). Concentration under reduced pressure and silica gel flash chromatography give the title compound as colorless oil. MS: 227 [M+H]+; tR (HPLC, CombiScreen ODS-AM 50×4.6 mm; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 2 min, flow 2.0 ml/min): 2.85 min.

Provenance & Evidence