Sulfuric Acid → 4-Methoxyphenylacetaldehyde

Participants

Reaction Steps

2.65 g of methyl 2-(p-methoxyphenyl)-1-methylthioethyl sulfoxide was dissolved in 50 ml. of methanol, and with the addition of 20 ml. of 1N sulfuric acid, the solution was heated for 6 hours at 50°C. The reaction mixture was concentrated at reduced pressure to 20 ml., and extracted with ether (150 ml., 2 times). The extracted layer was washed with water and then with an aqueous solution of sodium hydrogencarbonate, and dried with anhydrous sodium sulfate. It was then concentrated at reduced pressure, and the residue was subjected to column chromatography (silica gel, benzene and methylene chloride) to give 774 mg of p-methoxyphenylacetaldehyde as a colorless liquid. The yield was 53%, b.p. 61°-63°C/2.5 mmHg.

Provenance & Evidence