Hydrochloric Acid → [2-(Methoxymethyl)phenyl]methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,2-benzenedimethanol (1.38 g, 10 mmol) in DMF (10 mL) cooled in an ice bath is added NaH (400 mg, 60% in mineral oil, 10 mmol) in portions. The mixture is stirred at 0° C. for 15 min then at RT for 30 min. To this is added iodomethane (1.45 g, 10.2 mmol) dropwise and the mixture is stirred at RT for 1 h. Ice, EtOAc and water is added and the mixture is acidified with 1N HCl. The organic phase is washed with water and brine then is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by column chromatography using a gradient of 0-100% EtOAc/hexane as eluent to give the title compound.

Provenance & Evidence