Formic Acid → 3-Methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a round-bottomed flask equipped with magnetic stirring bar was charged DMF (5 mL) and triethylamine (2.81 g, 27.8 mmol). Next, 98% formic acid (1.28 g, 27.8 mmol) was added dropwise over 1 min. Then, 2a (1 g, 3.5 mmol) was added followed by Pd(OAc)2 (30 mg, 0.13 mmol) and DPPF (150 mg, 0.27 mmol). All the solids dissolved to give a clear orange solution. The mixture was then heated to 80° C. and after about 15 min a yellow solid precipitated. The mixture was cooled to room temperature and filtered. The filtrate was partitioned between Et2O (25 mL) and H2O (25 mL). The organic layer was further washed with H2O (25 mL) followed by brine. The organic phase was dried over anhydrous MgSO4 and evaporated under reduced pressure to yield a brown oil. Distillation under reduced pressure (0.1 torr) gave 3a as a colorless, mobile liquid (400 mg, 85%), lit. bp. 121° C./14 torr. 1H NMR (CDCl3): δ 9.97 (s, 1H), 7.47-7.42 (m, 2H), 7.39-7.37 (m, 1H), 7.20-7.14 (m, 1H), 3.86 (s, 3H); 13C NMR (CDCl3): δ 192.29, 160.38, 138.03, 130.22, 123.71, 121.70, 112.28, 55.67. Anal. Calcd for C8H8O2: C, 70.57; H, 5.92. Found: C, 70.27; H, 5.95.

Provenance & Evidence