Hydrochloric Acid → 2-Benzylacrylic Acid

To a cooled (0° C.) mixture of benzyl malonic acid (3.37 g, 17.4 mmol) and diethylamine (1.34 g, 18.3 mmol) in water (10 ml) was added formaldehyde (37% solution in water, 2.1 g, 26.1 mmol) with stirring. The reaction was allowed to warm to room temperature and after 2 hours heated to reflux. After 16 hours, the reaction mixture was cooled to room temperature, then made acidic with hydrochloric acid. The mixture was extracted twice with ethyl acetate. The ethyl acetate layers were combined and dried over sodium sulfate, then the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography to yield 2.2 g (78%) of white solid. 1H NMR (CDCl3): δ 3.7 (s, 2H), 5.6 (s, 1H), 6.4 (s, 1H), 7.1-7.4 (m, 5H)

1. temperatureTo a cooled
2. temperatureheated to reflux
3. temperaturethe reaction mixture was cooled to room temperature
4. extractionThe mixture was extracted twice with ethyl acetate
5. dry with materialdried over sodium sulfate
6. customthe solvent was removed under reduced pressure
7. customThe resulting residue was purified by column chromatography

ORD record

ord-1342a8b412324750a5f26c3072ae6588

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06288046B1