Sodium Thiosulfate → Methyl 2-(4-formylphenyl)acetate

Participants

Reaction Steps

To a stirring solution of Dess-Martin Periodinane (1.5 eq) in dichloromethane (0.3 M) at room temperature under nitrogen was added a solution of 29 in dichloromethane (0.2 M). After 4 hours the reaction was diluted with ether (0.1 M). The reaction mixture was then poured into a solution of sodium thiosulfate (10.5 eq) in saturated sodium bicarbonate (0.5 M) and stirred for 30 minutes. The phases were separated and the organic phase was washed with saturated sodium bicarbonate (1×), H2O (1×) and brine (1×) then dried over sodium sulfate, filtered and concentrated in vacuo to afford the product. (94%) 1H NMR (400 MHz, CDCl3) δ 10.00 (s, 1H), 7.86 (d, 2H), 7.46 (d, 2H), 3.72 (m, 5H).

Provenance & Evidence