4-Hydroxybenzaldehyde → 4-Formylphenyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

At 0° C., methanesulfonyl chloride (9.51 ml, 0.123 mol) was added to a solution of 4-hydroxybenzaldehyde (15 g, 0.123 mol) in pyridine (12.91 ml, 0.160 mol). The reaction mixture was stirred at 0° C. for 3 h and left at room temperature for 16 h. It was given onto conc. hydrochloric acid/ice (200 ml/200 ml). The mixture was extracted with ethyl acetate (4×300 ml). The combined organic layers were washed with a 5% aqueous solution of sodium hydrogen carbonate (3×200 ml) and brine (100 ml). They were dried over magnesium sulphate. The solvent was removed in vacuo to give 22.87 g of crude methanesulfonic acid 4-formylphenyl ester, which was used in the next step without further purification.

Provenance & Evidence