Hydrochloric Acid → 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxy-2(5H)-furanone

HRID 978225Notes

Reaction equation

HRID 978225 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].CO[C:15](OC)([CH3:17])[CH3:16].Cl>CC(C)=O>[CH3:16][C:15]1([CH3:17])[O:10][CH:9]([CH:7]2[O:8][C:2](=[O:1])[C:3]([OH:4])=[C:5]2[OH:6])[CH2:11][O:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 64952,2-DimethoxypropaneHCID 54670067L-Ascorbic Acid

Product 1

HCID 546765085-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxy-2(5H)-furanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 12-L round bottom flask was placed 8,000 mL acetone, 1,600 g L-ascorbic acid, 1,880 mL 2,2-dimethoxypropane and the mixture was stirred for 1/4 hr; hydrogen chloride was added slowly through bubbler over 2-4 min (color of solution changed from colorless to dark yellow). The mixture was stirred for 1 hr and became very viscous. The product was filtered, washed with cold acetone and the solid was then air dried in hood to give 1,521 g of 1st crop of 5,6-O-isopropylidene-L-ascorbic acid. The mother liquor was concentrated to give 225 g of 2nd crop and 162 g of 3rd crop of 5,6-O-isopropylidene-L-ascorbic acid.

Workup

  1. customIn a 12-L round bottom flask was placed
  2. filtrationThe product was filtered
  3. washwashed with cold acetone
  4. customair dried in hood

Sources & evidence

ORD record
ord-0e1f5b6b20524ca7ac6a0b07b93fa1cc
Source dataset
uspto-grants-1987_05
Patent number
US04663469

Reaction notes

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