4-Hydroxybenzaldehyde → 4-(((4-Methylphenyl)sulfonyl)oxy)benzaldehyde

Participants

Reaction Steps

To a solution of 4-hydroxybenzaldehyde (5.93 g, 48.56 mmol) and triethylamine (10 mL) in 50 mL of dichloromethane was added tosyl chloride (11.8 g, 61.89 mmol). The reaction mixture was stirred at room temperature for 24 hr. The reaction mixture was diluted with water, acidified with 1 N HCl, and extracted into methylene chloride. The organic layer was separated, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel chromatography (9:1 hexanes:ethyl acetate to 5:1 hexanes:ethyl acetate) to afford 9.50 g (71%) of the title compound of Step A. 1HNMR (CDCl3): δ 9.81 (s, 1H), 7.69 (d, 2H, J=8.8 Hz), 7.57 (d, 2H, J=8.4 Hz), 7.19 (d, 2H, J=8.4 Hz), 7.03 (d, 2H, J=8.4 Hz), and 2.28 (s, 3H).

Provenance & Evidence