Acetic Acid → HCID 54142678, compound

HRID 1734241Notes

Reaction equation

HRID 1734241 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=[O:3])C.[C:8]([O:11][CH2:12][C@@H:13]1[C@@H:17]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[O:16][CH2:15][O:14]1)(=[O:10])[CH3:9].[C:23](O)(=O)C>[Cl-].[Zn+2].[Cl-]>[C:5]([O:4][CH2:1][O:3][C@@H:13]([C@H:17]([O:16][C:15](=[O:14])[CH3:23])[CH2:18][O:19][C:20](=[O:22])[CH3:21])[CH2:12][O:11][C:8](=[O:10])[CH3:9])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 14157593HCID 14157593, compound

Product 1

HCID 54142678HCID 54142678, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

100 ml of acetic anhydride was added to 70.12 g of (4R,5R)-4,5-bis(acetoxymethyl)-1,3-dioxolane obtained in Example 4 and mixed at room temperature to dissolve. After the addition of 3.05 g of anhydrous zinc chloride and 10 ml of glacial acetic acid, the mixture was stirred overnight. The resultant reaction mixture was extracted with 700 ml of ethyl acetate, neutralized with saturated aqueous solution of sodium hydrogen carbonate, washed with water and saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and filtered. The solvent was removed by evaporation to obtain 99.48 g of the title compound as a reddish brown oil.

Workup

  1. additionmixed at room temperature
  2. dissolutionto dissolve
  3. customThe resultant reaction mixture
  4. extractionwas extracted with 700 ml of ethyl acetate
  5. washwashed with water and saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-9fdc587232564ee79b283d02e7e24ea4
Source dataset
uspto-grants-1996_07
Patent number
US05532380

Reaction notes

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