4-Hydroxybenzaldehyde → HCID 87309085, compound

Participants

Reaction Steps

To a solution of 2-chlorobenzothiazole (33.7 g, 199 mmol) in CH3CN (500 mL) was added 4-hydroxy benzaldehyde (24.3 g, 199 mmol) and K2CO3 (28 g, 199 mmol). The heterogeneous mixture was heated at reflux for 72 h and then cooled to rt. The solids were removed by filtration and washed with CH3CN (100 mL). To the filtrate was added an aqueous solution of NaHSO3 (26 g, 199 mmol, 66 mL water). After stirring for 3.5 h, the mixture was filtered and the wet cake was dried under vacuum overnight to afford the bisulfite complex (66 g, 92%) as a white powder. 1H NMR (500 MHz, DMSO-d6): 7.93 (d, J=8.0 Hz, 1H), 7.74 (d, J=8.0 Hz, 1H), 7.60-7.55 (m, 2H), 7.44-7.39 (m, 1H), 7.35-7.29 (m, 3H), 6.03 (d, J=5.2 Hz, 1H), 5.04 (d, J=5.2 Hz, 1H).

Provenance & Evidence