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Toluene → 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl chloride

HRID 413465
Notes
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Reaction equation

HRID 413465 reaction equation
C(O[C@@H:5]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.[Al+3].[Cl-:29].[Cl-].[Cl-].C1(C)C=CC=CC=1.[Si](O)(O)(O)O>C(Cl)(Cl)Cl>[CH3:26][C:25]([O:24][CH2:23][C@H:21]1[O:22][C@@H:5]([Cl:29])[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:11]([O:12][C:13]([CH3:14])=[O:15])[C@@H:16]1[O:17][C:18]([CH3:19])=[O:20])=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1140TolueneHCID 14942Orthosilicic acidHCID 2724702beta-D-Glucose pentaacetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 109595272,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl chloride

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent

Procedure

To a solution of β-D-glucose pentaacetate (20 g) in CHCl3 (100 mL) was added AlCl3 (3.6 g). After stirring at room temperature, toluene (100 mL) was added, followed by silicic acid (2 g). The mixture was stirred for a few minutes and the precipitate was removed by filtration. The solution was partially concentrated under vacuum and extracted with ice cold water (25 mL). The organic phase was concentrated to a syrupy mixture and ether was added to precipitate acetochloro-β-D-glucose as a powder (12 g).

Workup

  1. stirringThe mixture was stirred for a few minutes
  2. customthe precipitate was removed by filtration
  3. concentrationThe solution was partially concentrated under vacuum
  4. extractionextracted with ice cold water (25 mL)
  5. concentrationThe organic phase was concentrated to a syrupy mixture and ether
  6. additionwas added
  7. customto precipitate acetochloro-β-D-glucose as a powder (12 g)

Sources & evidence

ORD record
ord-13c042b451754b498daef7fb30167cd2
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06566508B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes