Isopropenyl acetate → 6-O-acetylascorbic acid

HRID 2209417Notes

Reaction equation

HRID 2209417 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)=C)(=[O:15])[CH3:14]>O1CCCC1>[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 7916Isopropenyl acetateHCID 54670067L-Ascorbic Acid

Product 1

HCID 546934696-O-acetylascorbic acidYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 tetrahydrofuran solution containing 4 g of ascorbic acid and 3 g of isopropenyl acetate, and then the reaction was continued for 22 hours at 40° C. The reaction mixture was then filtered, concentrated and recrystallized from acetone-benzene to yield 4.5 g of ascorbic acid-6-acetate. The water content of the reaction system was 700 ppm.

Workup

  1. customFour grams of the immobilized Lipase PS prepared by the same procedure as in Example 2
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated
  4. customrecrystallized from acetone-benzene

Sources & evidence

ORD record
ord-002b67edca0b41cc91588809d02fec50
Source dataset
uspto-grants-1995_10
Patent number
US05455174

Reaction notes

Loading…