Acetonitrile → acrylic acid 4-{3-[2-(1-chloro-9-oxo-9H-thioxanthen-4-yloxy)-acetoxy]-2-hydroxy-propoxy}-butyl ester

Participants

Reaction Steps

A reaction mixture containing (1-chloro-9-oxo-9H-thioxanthen-4-yloxy)-acetic acid (28.9 g, 0.09 mol), acetonitrile (345 mL), dimethylacetamide (240 ml), tetrabutylammonium bromide (2.9 g, 9 mmol), 2,6-di-tert-butyl-4-methylphenol (0.2 g, 0.9 mmol) and 4-hydroxybutylacrylate glycidylether (18.0 g, 0.09 mol) was heated to reflux. The mixture was allowed to stir at reflux temperature for 24 hours. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residual oil was dissolved in dichloromethane (400 mL) and extracted 3 times with a mixture of an aqueous solution of sodium hydroxide (1N) (200 mL) and distilled water (200 mL). The organic layer was isolated and dried over MgSO4. The solvent was evaporated to yield 15.7 g of a brown oil. Acrylic acid 4-{3-[2-(1-chloro-9-oxo-9H-thioxanthen-4-yloxy)-acetoxy]-2-hydroxy-propoxy}-butyl ester was purified on a Merck Super Vario Prep column using dichloromethane/ethyl acetate (75/25) as eluent, yielding 13.85 g of a yellow oil.

Provenance & Evidence