Acetic Acid → HCID 22399559, compound

HRID 1734247Notes

Reaction equation

HRID 1734247 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=[O:3])C.[C:8]([O:11][CH2:12][CH:13]1[CH: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][CH:13]([CH: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 14157591HCID 14157591, compound

Product 1

HCID 22399559HCID 22399559, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

20 ml of acetic anhydride was added to 12.2 g of (4RS,5SR)-4,5-bis(acetoxymethyl)-1,3-dioxolane obtained in Example 20. The mixture was mixed to dissolution at room temperature. To this were added 0.7 g of anhydrous zinc chloride and 2 ml of glacial acetic acid. The mixture was stirred overnight at room temperature and extracted with 300 ml of ethyl acetate. The extract was neutralized with saturated aqueous solution of sodium hydrogen carbonate. After washing with water and drying over anhydrous sodium sulfate, the product was filtered and the solvent was evaporated to obtain 19.0 g (yield: 92.0%) of the title compound.

Workup

  1. additionThe mixture was mixed to dissolution at room temperature
  2. extractionextracted with 300 ml of ethyl acetate
  3. washAfter washing with water
  4. dry with materialdrying over anhydrous sodium sulfate
  5. filtrationthe product was filtered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-94aa4142253041eb978bf22544ce1c7d
Source dataset
uspto-grants-1996_07
Patent number
US05532380

Reaction notes

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