Dimethyl Sulfoxide → 2-(4-Chlorophenyl)-2-methylpropanal

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Reaction Conditions

Reaction Steps

The DMSO (436 mL, 61.4 mmol) was dissolved in 100 mL of DCM and treated with oxalyl chloride (4.02 μL, 46.6 mmol) at −78° C. The solution stirred for 30 minutes at −78° C. before the 2-(4-chlorophenyl)-2-methyl-propan-1-ol (5.67 g, 30.7 mmol) was added dropwise as a solution in 10 mL of DCM. After addition was complete, the solution was stirred for two hours at −78° C., and then treated with triethyl amine (25.7 mL, 184 mmol). The solution was allowed to warm to ambient temperature and stir for three hours. The solution was quenched with the addition of water and partitioned with more DCM. The aqueous was extracted with DCM, and the combined organics were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography (silica, hexanes/ethyl acetate gradients) to afford 2-(4-chlorophenyl)-2-methylpropionaldehyde as a yellow oil (5.60 g, 99%). 1H NMR (CDCl3, 400 MHz) δ 9.48 (s, 1H), 7.35 (d, J=8.8 Hz, 2H), 7.21 (d, J=8.8 Hz, 1H), 1.45 (s, 6H).

Provenance & Evidence