Benzene → HCID 15814063, compound

HRID 1734239Notes

Reaction equation

HRID 1734239 reaction equation
[C:1]([Br:4])(=[O:3])C.[C:5]([O:8][CH2:9][C@@H:10]1[C@@H:14]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:13][CH2:12][O:11]1)(=[O:7])[CH3:6].[CH:20]1C=CC=CC=1>[Cl-].[Zn+2].[Cl-]>[Br:4][CH2:1][O:3][C@@H:10]([C@H:14]([O:13][C:12](=[O:11])[CH3:20])[CH2:15][O:16][C:17](=[O:19])[CH3:18])[CH2:9][O:8][C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 241BenzeneHCID 10482Acetyl bromideHCID 14157593HCID 14157593, compound

Product 1

HCID 15814063HCID 15814063, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A mixture of 25.0 g of acetyl bromide and 42.0 g of (4R,5R)-4,5-bis(acetoxymethyl)-1,3-dioxolane obtained in Example 4 was stirred under cooling with ice, and 1.0 g of anhydrous zinc chloride was added to it. After the reaction for 30 minutes, the ice water bath was dismantled and the mixture was stirred for a further one hour while stirring at room temperature. After the reaction, 50 ml of benzene was added to separate insoluble matters by filtration, and the benzene was evaporated at a low temperature (below room temperature). No peaks for the raw material were observed at all by NMR analysis of the reaction product, indicating that the decylization occurred quantitatively and the title compound was produced.

Workup

  1. additionwas added to it
  2. customAfter the reaction for 30 minutes
  3. stirringthe mixture was stirred for a further one hour
  4. stirringwhile stirring at room temperature
  5. additionwas added
  6. customto separate insoluble matters
  7. filtrationby filtration
  8. customthe benzene was evaporated at a low temperature (below room temperature)

Sources & evidence

ORD record
ord-146d69ee01534e39bef6252909f41707
Source dataset
uspto-grants-1996_07
Patent number
US05532380

Reaction notes

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