Hydrochloric Acid → HCID 86605980, compound

HRID 2061328Notes

Reaction equation

HRID 2061328 reaction equation
C([O:4][C:5]1[CH:42]=[CH:41][C:8]([CH2:9][C:10]2[CH:15]=[C:14]([C@:16]3([O:34][C@H:33]([CH2:35][O:36]C(=O)C)[C@@H:28]([O:29]C(=O)C)[C@H:23]([O:24]C(=O)C)[C@H:18]3[O:19]C(=O)C)[OH:17])[CH:13]=[CH:12][C:11]=2[CH3:40])=[CH:7][CH:6]=1)(=O)C.[OH-].[K+].Cl>CO.O1CCCC1>[OH:17][C@:16]1([C:14]2[CH:13]=[CH:12][C:11]([CH3:40])=[C:10]([CH2:9][C:8]3[CH:7]=[CH:6][C:5]([OH:4])=[CH:42][CH:41]=3)[CH:15]=2)[O:34][C@H:33]([CH2:35][OH:36])[C@@H:28]([OH:29])[C@H:23]([OH:24])[C@H:18]1[OH:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86649087HCID 86649087, compound

Product 1

HCID 86605980HCID 86605980, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-acetoxybenzyl)-1-methyl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-benzene (1.8 g) in a mixture of methanol (30 mL) and tetrahydrofuran (15 mL) is treated with aqueous potassium hydroxide solution (4 mol/L, 3.8 mL). The reaction solution is stirred at ambient temperature for 30 min and then neutralized with hydrochloric acid (1 mol/L). The resulting mixture is concentrated under reduced pressure, diluted with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic phases are dried (sodium sulphate) and concentrated.

Workup

  1. concentrationThe resulting mixture is concentrated under reduced pressure
  2. additiondiluted with aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried (sodium sulphate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e7121f6ccb914990b05ad8d7e6a38af3
Source dataset
uspto-grants-2012_10
Patent number
US08283326B2

Reaction notes

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