Vinyl Acetate → 6-O-acetylascorbic acid

HRID 2209416Notes

Reaction equation

HRID 2209416 reaction equation
[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]([OH:6])=[C:3]1[OH:4].[C:13](OC=C)(=[O:15])[CH3:14]>C(O)(C)(C)C>[C:13]([O:12][CH2:11][C@H:9]([OH:10])[C@H:7]1[O:8][C:2](=[O:1])[C:3]([OH:4])=[C:5]1[OH:6])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 54670067L-Ascorbic Acid

Product 1

HCID 546934696-O-acetylascorbic acidYield 96.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Four grams of the immobilized Lipase PS prepared by the same procedure as in Example 2 was added to 40 ml of a dry t-butanol solution containing 4 g of ascorbic acid and 3 g of vinyl acetate. The reaction was continued for 20 hours at 50° C. The reaction mixture was filtered and concentrated to yield 4.8 g of a crude ascorbic acid-6-acetate. Recrystallization from acetone-benzene gave a crystal with purity of 93%. The water content of the reaction system was 650 ppm.

Workup

  1. customFour grams of the immobilized Lipase PS prepared by the same procedure as in Example 2
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-433b11e2f84e42e3b2bedb133b0519b6
Source dataset
uspto-grants-1995_10
Patent number
US05455174

Reaction notes

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