Acetyl chloride → Methyl 4-Formylbenzoate

Participants

Reaction Steps

4-Carboxybenzaldehyde (2 mmol) was diluted in 6 mL of anhydrous MeOH. The mixture under N2 was placed in an ice bath and acetyl chloride (10 mmol) was added dropwise. The ice bath was removed and the mixture was stirred overnight at room temperature. The methanol was removed under reduced pressure and the mixture was diluted in 35 mL of EtOAc. The organic phase was washed with 5×10 mL of 1N NaOH and 3×10 mL of brine, dried with MgSO4 and filtered. The volatiles were removed and the product was obtained as a pale yellow solid (96% yield). mp 142-144° C. 1H RMN (CDCl3) δ10.04 (s, 1H), 8.13 (d, 2H, J=8.2 Hz), 7.89 (d, 2H, J=8.1 Hz), 3.90 (s, 3H). 13C NMR (CDCl3) δ 191.91, 166.26, 139.35, 135.27, 130.40, 129.74, 52.81. HRMS (FAB) calcd for C9H9O3 ([M+H]+): 165.0546. found 165.0543.

Provenance & Evidence