Tetrahydrofuran → 3,4-Dimethoxybenzeneacetaldehyde

Participants

Reaction Steps

1.80 g of isopropyl isopropylthiomethyl sulfoxide was dissolved in 15 ml. of tetrahydrofuran, and under cooling with ice, 240 mg of sodium hydride was added, and the solution was stirred for one hour. 2.31 g of 3,4-dimethoxybenzyl bromide was added, and the mixture was stirred for 20 hours at room temperature, and for 3 hours at 35°C. 100 ml. of methylene chloride was added. After separating the insoluble water by filtration, the filtrate was concentrated at reduced pressure. The residue was dissolved in 20 ml. of tetrahydrofuran, and with the addition of 10 drops of concentrated sulfuric acid, the solution was stirred for 10 hours at 50°C. 500 mg of sodium bicarbonate was added, and the mixture was stirred for 30 minutes at room temperature. Then, the insoluble matter was separated by filtration. The filtrate was concentrated at reduced pressure, and the residue was subjected to column chromatography to give 631 mg of (3,4-dimethoxyphenyl)acetaldehyde in a yield of 35%.

Provenance & Evidence