4-Methoxyphenol → Galactosyloxyethylacrylate

反応式

[CH3:1][O:2][C@H:3]1[O:8][CH:7]([CH2:9][OH:10])[C@H:6]([OH:11])[C@@H:5]([OH:12])[C@@H:4]1[OH:13].[CH3:14][O:15][C:16]1C=CC(O)=[CH:18][CH:17]=1.[OH-:23].[Na+]>C(OCCO)(=O)C(C)=C>[C:16]([O:15][CH2:14][CH2:1][O:2][CH:3]1[O:8][C@H:7]([CH2:9][OH:10])[C@H:6]([OH:11])[C@H:5]([OH:12])[C@H:4]1[OH:13])(=[O:23])[CH:17]=[CH2:18]

参加物

実験手順

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%).