1-Butanol → L-Ascorbic Acid

HRID 1531428Notes

Reaction equation

HRID 1531428 reaction equation
[CH2:1]([OH:13])[C@H:2]([OH:12])[C@@H:3](O)[C@H:4]([OH:10])[C:5]([C:7]([OH:9])=[O:8])=[O:6].ClC(Cl)=C(Cl)Cl.C(O)CCC.S(=O)(=O)(O)O.Cl>>[OH:10][C:4]1[C@@H:3]([C@@H:2]([OH:12])[CH2:1][OH:13])[O:8][C:7](=[O:9])[C:5]=1[OH:6]

Participants

6

Reactant 5

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 31373Tetrachloroethylene2×HCID 1024242-keto-L-Gulonic acid

Product 1

HCID 54670067L-Ascorbic Acid

Conditions

Temperature
85 °C

Procedure

594 g (3 mol) of anhydrous 2-keto-L-gulonic acid were suspended in a solvent mixture consisting of 72 ml (0.7 mol) of perchloroethylene and 1 l (11 mol) of n-butanol. After addition of 7 g (69 mmol) of conc. sulfuric acid, the mixture was evacuated to 300 mbar and heated to an internal temperature of 85° C. The distillate was removed. After 2 hours, 24 ml of water were removed. After addition of 725 ml (7 mol) of fresh perchloroethylene, the viscous reaction mixture was rapidly treated with 79 g (0.8 mol) of conc. hydrochloric acid and stirred at 75° C. for 17 hours. The precipitated L-ascorbic acid was filtered off with suction, washed with n-butanol and dried in vacuo. Yield: 460 g (86%) of a gray crystallizate having a vitamin C purity of 99%. Vitamin C of high purity can be obtained by processes known from the literature, e.g. recrystallization.

Workup

  1. customthe mixture was evacuated to 300 mbar
  2. customThe distillate was removed
  3. custom24 ml of water were removed
  4. filtrationThe precipitated L-ascorbic acid was filtered off with suction
  5. washwashed with n-butanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-0c0687653d48482bab6def0383c8d6af
Source dataset
uspto-grants-2001_03
Patent number
US06197977B1

Reaction notes

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