Methanol → Phenyl beta-D-galactopyranoside

HRID 1250759Notes

Reaction equation

HRID 1250759 reaction equation
CC([O:4][CH2:5][C@H:6]1[O:11][C@@H:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]([O:19]C(C)=O)[C@@H:8]([O:23]C(C)=O)[C@H:7]1[O:27]C(C)=O)=O.CO.C[O-].[Na+]>C(O)(=O)C>[CH:16]1[CH:15]=[CH:14][C:13]([O:12][C@@H:10]2[O:11][C@H:6]([CH2:5][OH:4])[C@H:7]([OH:27])[C@H:8]([OH:23])[C@H:9]2[OH:19])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 102346Phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosideHCID 10942334Sodium Methoxide

Product 1

HCID 102336Phenyl beta-D-galactopyranosideYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To phenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (21.2 g) were added methanol (120 ml) and 28% sodium methylate (0.28 ml) and the mixture was refluxed with stirring for 5 hours. After the reaction solution was cooled, acetic acid (0.1 ml) was added and the mixture was stirred for 30 minutes. Concentration of the reaction solution and crystallization with ethanol (180 ml) gave 9.8 g (yield 77%) of phenyl-β-D-galactopyranoside. Melting point: 154.5° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureAfter the reaction solution was cooled
  3. stirringthe mixture was stirred for 30 minutes
  4. customConcentration of the reaction solution and crystallization with ethanol (180 ml)

Sources & evidence

ORD record
ord-f26a427a205947ca8efaa64c8cab0541
Source dataset
uspto-grants-2002_01
Patent number
US06339162B1

Reaction notes

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