2-Hydroxyethyl acrylate → Galactosyloxyethylacrylate

HRID 1681704Notes

Reaction equation

HRID 1681704 reaction equation
[CH3:1][O:2][C@@H: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].CC1C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=1.[OH-].[Na+].[C:32]([O:36][CH2:37]CO)(=[O:35])[CH:33]=[CH2:34]>OP(O)=O.O[Mo](O)(=O)=O>[CH:3]1([O:2][CH2:1][CH2:37][O:36][C:32](=[O:35])[CH:33]=[CH2:34])[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]

Participants

6

Reactant 4

HCID 131652-Hydroxyethyl acrylateHCID 14798Sodium HydroxideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 94214methyl beta-D-galactopyranoside

Product 1

HCID 18648933Galactosyloxyethylacrylate

Reagents, catalysts & solvents 1

HCID 21863154Dihydroxy(dioxo)molybdenum;phosphonic acidCatalyst

Procedure

A 20.0 g quantity of methyl β-D-galactoside (product of Nacalai Co., Ltd., a guaranteed reagent)was suspended in 150 ml of 2-hydroxyethyl acrylate. To the suspension were added 1.0 g of butylhydroxytoluene and 1.0 g of phosphomolybdic acid, and the mixture was stirred well and gradually heated. After heating to a temperature of 60° to 70° 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 purified in the same manner as in Example 1. A fraction (Rf =0.2) of the reaction mixture was concentrated, giving 15.8 g of galactosyloxyethylacrylate (HEA-Gal) as an oily product (yield 55%).

Workup

  1. temperaturegradually heated
  2. temperatureAfter heating to a temperature of 60° to 70° C.
  3. stirringthe mixture was further stirred for about 2 hours
  4. temperaturewhile maintaining the same temperature
  5. customThe obtained reaction mixture
  6. customwas purified in the same manner as in Example 1
  7. concentrationA fraction (Rf =0.2) of the reaction mixture was concentrated

Sources & evidence

ORD record
ord-879118f02449472f9ea9935d68056fe2
Source dataset
uspto-grants-1992_12
Patent number
US05173554

Reaction notes

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