Dimethylformamide → 3,3-Dimethyl-2,3-dihydrobenzofuran-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

Phosphorus oxychloride (30.6 g, 0.2 mole) was added dropwise to a mixture of dimethyl formamide (14.6 g, 0.2 mole) and 2,3-dihydro-3,3-dimethyl benzofuran (14.8 g, 0.1 mole) over half an hour. The temperature rose to 55° C. during addition. The temperature was then raised to 100° C. and maintained for 1 hour prior to addition to a hot solution of sodium acetate (75 g) in water (75 ml). After cooling, the organic layer was separated, dried and distilled yielding 5.6 g unchanged starting material bp 35°-40° C. at 0.1 mm and 5.2 g aldehyde bp 85° C. at 0.1 mm. The product contained a little 2,2-dimethyl isomer from the previous stage.

Provenance & Evidence