Thionyl Chloride → Methyl 5-cyano-2-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 5-((hydroxyimino)methyl)-2-methoxybenzoate (1.04 g, 4.94 mmol) was dissolved in methylene chloride (25 mL) and cooled to 0° C. The reaction was treated with thionyl chloride (0.59 mL, 8.1 mmol) and stirred at 0° C. for 2 h. After warming to room temperature, the reaction was diluted with methylene chloride, washed with saturated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated to afford 0.87 g (92%) which was used without further purification. 1H-NMR (CDCl3, 500 MHz) δ 8.09 (d, J=2.1 Hz, 1H), 7.75 (dd, J=8.9, 2.1 Hz, 1H), 7.05 (d, J=8.9 Hz, 1H), 3.96 (s, 3H), 3.90 (s, 3H). Mass spec.: 192.02 (MH)+.

Provenance & Evidence