Sodium Hydroxide → 2-(4-carboxybenzyl)phenyl beta-D-glucopyranoside

HRID 1982827Notes

Reaction equation

HRID 1982827 reaction equation
[O:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([O:28]C)=[O:27])=[CH:22][CH:21]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[OH-].[Na+]>CO>[O:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([OH:28])=[O:27])=[CH:22][CH:21]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 674597572-(4-methoxycarbonylbenzyl)phenyl beta-D-glucopyranoside

Product 1

HCID 674584912-(4-carboxybenzyl)phenyl beta-D-glucopyranosideYield 78.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(methoxycarbonyl)benzyl]phenyl β-D-glucopyranoside (0.050 g) in methanol (1 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.26 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by column chromatography on (benzenesulfonylpropyl) silica gel (eluent: methanol) to give 2-(4-carboxybenzyl)phenyl β-D-glucopyranoside (0.038 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on (benzenesulfonylpropyl) silica gel (eluent: methanol)

Sources & evidence

ORD record
ord-cb6c5cbc45d940d39b488048a247f00a
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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