Formaldehyde → Ethyl 2-benzylacrylate

Participants

Reaction Steps

N-butyl lithium (201 ml of 1.6M) was added dropwise to diisopropyl amine (45 ml) in dry tetrahydrofuran (870 ml) at -78° C. After stirring at this temperature for 0.5 hours ethyl-2-benzylacetoacetate (39.6 g, 0.18M) in THF (250 ml) was added dropwise at 0° C. After stirring for 20 minutes, paraformaldehyde (35.42 g) was added at room temperature followed by stirring for one hour and refluxing for 4 hours. The reaction mixture was filtered and the liquid evaporated to dryness. The residue was dissolved in a mixture of KHCO3 /H2O and methylene chloride (1:1) and stirred for 0.5 hours. The layers were separated and the methylene chloride layer was dried over K2CO3 and then evaporated to dryness to yield 46.4 g of named product. This product was purified with a Prep-500 chromatograph eluting with hexane to 5% ethyl acetate/hexane gradient to yield 30 g of a clear liquid. ms (fd)= 190M+

Provenance & Evidence