4-Methoxyphenol → Galactosyloxyethylacrylate

HRID 1681703Notes

Reaction equation

HRID 1681703 reaction equation
[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]

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 14798Sodium HydroxideHCID 76607Methyl glucoside

Product 1

HCID 18648933Galactosyloxyethylacrylate

Reagents, catalysts & solvents 1

HCID 133602-Hydroxyethyl MethacrylateSolvent

Procedure

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%).

Workup

  1. temperaturegradually heated
  2. temperatureAfter heating to a temperature of 80° to 90° C.
  3. stirringthe mixture was further stirred for about 2 hours
  4. temperaturewhile maintaining the same temperature
  5. customThe obtained reaction mixture
  6. concentrationwas concentrated under reduced pressure
  7. concentrationA fraction (Rf =0.2) of the reaction mixture was concentrated

Sources & evidence

ORD record
ord-4f6ec57f24914b149cbc1725a4f5dfe6
Source dataset
uspto-grants-1992_12
Patent number
US05173554

Reaction notes

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