Sodium Bicarbonate → 6-Bromo-2-hydroxy-3-methoxybenzaldehyde

Participants

Reaction Steps

To the aldehyde 11 (17.7 g) in aqueous methanol (125 mL) was added sodium bicarbonate (7.6 g, 1.1 eq.) and the turbid bright yellow solution stirred for 2 hours. The solution was acidified, extracted with dichloromethane and the solvent removed in vacuo to afford a yellow solid. The product was recrystallized from ethyl acetate/hexane to afford yellow crystals (14.7 g, 98%): m.p. 105.6-106.4° C., lit19 m.p. 102-103° C.; EIMS m/z 232 (M+, 81Br), 230 (M+, 79Br), 186, 107, 79, 54, 32; Anal. Calcd. For C8H7O3Br: C, 41.59; H, 3.05. Found: C, 41.83; H, 3.27.

Provenance & Evidence