4-Hydroxybenzaldehyde → Methyl 2-(4-formylphenoxy)acetate

Participants

Reaction Steps

To a solution of 4-hydroxybenzaldehyde (100 g, 0.818 mol) in dry DMF (1 L) was added potassium carbonate (260 g, 1.88 mol) and KI (10 g) with stirring at rt. The reaction mixture was slowly heated to 40° C. and added methylbromoacetate (104 g, 0.67 mol) with stirring and heated to 70° C. for 4 h. The reaction mixture was cooled to rt, filtered off the solid and filtrate was diluted with water (1.5 L). The aqueous mixture was extracted with EtOAc (3×750 mL), washed with 2.5% aqueous NaOH solution (2×400 mL), water and dried. The solvent was removed under vacuum to give the title compound a slight yellow solid (112 g).

Provenance & Evidence