3-Hydroxybenzaldehyde → 3-Hydroxybenzyl alcohol

Participants

Reaction Steps

NaBH4 (775 mg, 20.5 mmol) is gradually added to a solution of 3-hydroxybenzaldehyde (5 g, 40.9 mmol) in EtOH (25 mL) while cooling the reaction mixture with cold water. This mixture is stirred for 5-10 min at the same temperature. And then dichloromethane (DCM) (100 mL) is added followed by a 2M HCl aqueous solution (until pH ˜3). The organic phase is separated and the final product is extracted 4 times from the aqueous phase with a EtOH/DCM mixture in the proportion of 1:3. The collected organic phases are dried on Na2SO4. After evaporation of the solvents under reduced pressure, a viscous colorless oil is obtained (4.9 g, 97%), which gradually crystallizes.

Provenance & Evidence