Water → 2-(4-methoxybenzyl)-3,5-dimethylphenyl beta-D-glucopyranoside

HRID 1247761Notes

Reaction equation

HRID 1247761 reaction equation
C([O:4][C@@H:5]1[C@@H:28]([O:29]C(=O)C)[C@H:27]([O:33]C(=O)C)[C@@H:26]([CH2:37][O:38]C(=O)C)[O:25][C@H:6]1[O:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=O)C.[OH-].[Na+].O>C(O)C>[O:7]([C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[C@@H:6]1[O:25][C@H:26]([CH2:37][OH:38])[C@@H:27]([OH:33])[C@H:28]([OH:29])[C@H:5]1[OH:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 120856042-(4-methoxybenzyl)-3,5-dimethyl-phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Product 1

HCID 99530532-(4-methoxybenzyl)-3,5-dimethylphenyl beta-D-glucopyranosideYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(4-methoxybenzyl)-3,5-dimethyl-phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (7.4 g) in ethanol (150 mL) was added 2 mol/L aqueous sodium hydroxide solution (65 mL), and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 2-(4-methoxybenzyl)-3,5-dimethylphenyl β-D-glucopyranoside (5.2 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d0249565b92049838a1226cce019841d
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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