Dimethylformamide → 2,3-Dihydro-1,4-benzodioxine-5-carbaldehyde

Participants

Reaction Steps

Into a 100 ml round bottom flask fitted with a nitrogen gas inlet, condenser, and a magnetic stirring bar were placed 2,3-dihydroxybenzaldehyde (4.00 g, 29.0 mmol), 70 ml anhydrous dimethylformamide, and cesium carbonate (14.15 g, 43.5 mmol). The mixture was heated to 110° and stirred for 2.5 hours. The reaction was allowed to cool to room temperature and ethyl acetate was added. This solution was washed four times with brine, dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed (0-10% ethyl acetate/hexanes to give 4.07 g of subtitled product (86%) which was used directly in the next step.

Provenance & Evidence