Sodium Bicarbonate → Methyl 2-(4-formylphenyl)-2-methylpropanoate

Participants

Reaction Conditions

Reaction Steps

To an ambient temperature solution of 2-(4-Bromomethyl-phenyl)-2-methyl-propionic acid methyl ester (275 mg, 1.01 mmol) in DMSO (8 mL) is added sodium bicarbonate (127 mg, 1.52 mmol). The reaction mixture is heated to 120° C. After 3 h, the reaction is concentrated and the residue is partitioned between EtOAc and NaHCO3. The aqueous layer is extracted with EtOAc and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 20% EtOAc/Hex) to yield the title compound (179 mg, 86%). 1H NMR (400 MHz, CDCl3) δ 10.00 (s, 1H), 7.85 (d, 2H, J=8.4 Hz), 7.50 (d, 2H, J=8.4 Hz), 3.67 (s, 3H), 1.61 (s, 6H).

Provenance & Evidence