4-Methoxyphenol → Galactosyloxyethylacrylate

Participants

Reaction Steps

A 19.4 g quantity of methyl glucoside (STA-MEG 106, product of Horizon Chemical A. E. Staley Manufacturing Co.) was suspended in 140 ml of 2-hydroxyethyl methacrylate. To the suspension were added 2.6 g of hydroquinone monomethyl ether and 1.0 g of phosphomolybidic acid, and the mixture was stirred well and gradually heated. After heating to a temperature of 80° to 90° C., the mixture was further stirred for about 2 hours while maintaining the same temperature and was neutralized with 2N sodium hydroxide. The obtained reaction mixture was concentrated under reduced pressure and subjected to silica gel chromatography (eluent, chloroform:methanol=9:1). A fraction (Rf =0.2) of the reaction mixture was concentrated, giving 20.1 g of galactosyloxyethyl acrylate (HEMA-Glc) as an oily product (yield 68.8%).

Provenance & Evidence