Hydrochloric Acid → 1-Chloro-4-(beta-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene

HRID 1443760Notes

Reaction equation

HRID 1443760 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][O:28]C(=O)C)[C@@H:20]([O:21]C(=O)C)[C@H:15]([O:16]C(=O)C)[C@H:10]2[O:11]C(=O)C)[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39]C(=O)C)=[CH:35][CH:34]=1.[OH-].[K+].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][OH:28])[C@@H:20]([OH:21])[C@H:15]([OH:16])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:34]=[CH:35][C:36]([OH:39])=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86608492HCID 86608492, compound

Product 1

HCID 866006741-Chloro-4-(beta-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7.9 g 1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-(4-acetoxy-benzyl)-benzene in 150 mL methanol is added 25 mL 4 M aqueous potassium hydroxide solution. The solution is stirred at room temperature for 1 h and then adjusted to pH 5 with 4 M hydrochloric acid. Most of the methanol is evaporated and the remaining solution is extracted with ethyl acetate. The combined extracts are dried over sodium sulfate and the solvent is removed in vacuo.

Workup

  1. customMost of the methanol is evaporated
  2. extractionthe remaining solution is extracted with ethyl acetate
  3. dry with materialThe combined extracts are dried over sodium sulfate
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-ca803501f7274fdd8e3a8e6b65a99e9f
Source dataset
uspto-grants-2010_02
Patent number
US07662790B2

Reaction notes

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