Dimethylacetamide → Butyl 3-(4-formylphenyl)prop-2-enoate

Participants

Reaction Steps

20.4 g (110 mmol) of 4-bromobenzaldehyde A1, 19.7 g (154 mmol) of nbutylacrylate D1, 10 mg (0.05 mmol) of 2,6-di- tert-butylphenol and 9.9 g (120 mmol) of sodium acetate are mixed with 200 ml of dimethylacetamide and, after adding 5 ppm each of the catalysts K1-K11 (1.2), are stirred for 90 minutes at 190° C. in an oil bath. The mixture is worked up in water and extracted with ether. The organic phases are washed several times with water and are filtered through silica gel. The solvent is evaporated, giving 4-formylcinnamic acid-n-butyl ester C25 (purity>99% GC) without any purification in a yield of >95%. Analytical data identical with the described data (J. Organomet. Chem, 1995, 491, 1-2, C1; Angew. Chem., 1995, 107, 1989). Molecular mass C14H16O3: 232.28; calcd. C: 72.39%, H: 6.94%; found C: 72.46%, H: 7.00%.

Provenance & Evidence