o-Vanillin → HCID 13400171, compound

Participants

Reaction Steps

To a stirred suspension containing 2-hydroxy-3-methoxybenzaldehyde (4.0 g, 26.3 mmol) and K2CO3 (4.36 g, 31.60 mmol) in DMF (15 mL), bromoacetaldehyde diethyl acetal (4.86 mL, 31.60 mmol) was added dropwise. The mixture was refluxed for 4 h. After cooling, the precipitate was filtered off and the solvent was evaporated in vacuo. The crude residue was adsorbed on silica gel and purified by flash chromatography eluting with hexane/EtOAc (4:1) to give 28 (2.60 g, 36%). 1H NMR (500 MHz, CDCl3): δ: 10.53 (1H, s, CHO), 7.42 (1H, m, ArH), 7.14-7.12 (2H, m, ArH), 4.83 (1H, t, J=5.30 Hz, CH), 4.21 (2H, d, J=5.35 Hz, CH2), 3.90 (3H, s, OCH3), 3.74-3.71 (2H, m, CH2CH3), 3.60-3.57 (2H, m, CH2CH3), 1.22 (6H, t, J=7.05 Hz, 2×CH3).

Provenance & Evidence