Triethylamine → 3-Chloro-4-methylbenzaldehyde

Participants

Reaction Steps

To a solution of 3-chloro-4-methylbenzyl alcohol (2.00 g) and triethylamine (8.9 ml) in dimethyl sulfoxide (10 ml) was added sulfur trioxide-pyridine complex (4.47 g) under water-cooling. The mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into ice water and the mixture was extracted with diethyl ether. The organic layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution and dried over magnesium sulfate. The residue was concentrated to dryness under reduced pressure to give 3-chloro-4-methylbenzaldehyde (1.40 g) as a pale-yellow oil.

Provenance & Evidence