Benzyl Chloride → 3-Benzyloxy-4-hydroxybenzaldehyde

Participants

Reaction Steps

3,4-Dihydroxybenzaldehyde (30.2 g, 219 mmol) is dissolved in DMF (300 mL) and added to a suspension of NaH (60% oil, 17.2 g, 430 mmol) in DMF (500 mL) at RT. The mixture is stirred for 30 minutes and benzyl chloride (17.3 mL, 150 mmol) is added at 0° C. The reaction is stirred overnight. The solvent is removed by evaporation and the residue is dissolved in water (500 mL). The mixture is extracted three times with CH2Cl2. The aqueous layer is acidified with HOAC (100 mL). The product is precipitated and filtered, washed with water to provide 3-benzyloxy-4-hydroxybenzaldehyde.

Provenance & Evidence