Acetic Anhydride → HCID 11806680, compound

Participants

Reaction Steps

2,4,6-Trihydroxybenzaldehyde (4) (4.62 g, 30 mmol), acetic anhydride (6.13 g, 60 mmol) and a catalytic amount of N,N-dimethylaminopyridine (DMAP) in dry ethyl acetate (EtOAc) (100 mL) were refluxed overnight. The reaction mixture was filtrated, water (50 mL) was added and the water phase extracted with EtOAc (4×25 mL). The combined organic phases were washed with water (2×25 mL) and dried (MgSO4). The crude product was recrystallized from 1,2-dimethoxyethane (DME) to give the titled compound as white crystals, m.p. 103-105° C. Yield 4.3 g. (60%). 1H NMR (300 MHz, CDCl3): δ=2.29 (3H, s), 2.36 (3H, s), 6.61 (1H, s), 6.63 (1H, s), 10.04 (1H, s), 11.77 (1H, s); 13C NMR (75 MHz): δ=20.6 (CH3), 21.0 (CH3), 107.6 (CH), 108.1 (CH), 111.0 (C), 153.5 (C), 157.2 (C), 163.9 (C), 169.7 (C═O), 168.1 (C═O), 191.8 (HCO).

Provenance & Evidence