N,N-Dimethylaniline → 3',5'-Dimethoxybenzoin acrylate

Participants

Reaction Steps

To an ice cooled solution of 0.8 g (2.94 mmoles) of 3',5'-dimethoxybenzoin prepared in (3) above and 1.13 ml dimethylaniline in 10 ml methylene chloride, under nitrogen, was slowly added a solution of 1.5 ml (18 mmoles) acryloyl chloride in 10 ml of mehtylene chloride. After the addition was complete, the mixture was stirred overnight at room temperature, diluted with methylene chloride, washed twice with 75 ml 5% aqueous HCl, once with 100 ml H2O, once with 100 ml 5% aqueous NaHCO3, once with 100 ml H2O, once with 100 ml saturated Na2SO4 and dried over anhydrous Na2SO4. The solvent was filtered and stripped off to yield an oil that crystallized to give 0.6 g (63%) of compound. Recrystalization from benzene/hexane (1/1) gave colorless crystals, mp 88°-89° C. Infrared, NMR, and mass spectrometric analyses showed that the above compound was obtained.

Provenance & Evidence