Chloroacetonitrile → 5,6-Dimethoxy-2,3-dihydrobenzofuran-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

2-Hydroxy-4,5-dimethoxybenzaldehyde (25.5 g, 0.14 mol), chloroacetonitrile (12.4 g, 0.168 mol) and potassium carbonate (116 g, 0.84 mol) was dissolved in DMF (150 ml). The mixture was stirred for 10 minutes at 165° C. The solvent was concentrated under reduced pressure. The residue was separated in two parts, water was added and the first part was extracted with diethyl ether and the second part extracted with DCM. The second part was evaporated under reduced pressure and dissolved in ether and washed once with water. The organic layers was combined and evaporated under reduced pressure. The crystalline residue was washed with warm methanol (700 ml) and filtered. The residue was dissolved in 225 ml DCM and diethyl ether (450 ml) was added. The crystals formed was collected giving 14.6 g (51% yield) of product. Mp. 162° C.

Provenance & Evidence