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

HRID 1285539Notes

Reaction equation

HRID 1285539 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

The mixture of 80 ml of acetone, 16 g of L-ascorbic acid and 18.8 ml of 2,2-dimethoxypropane was stirred for 15 minutes at room temperature. Hydrogen chloride was added slowly through bubbler to the reaction mixture over 5 minutes and the mixture was stirred for 1 hr at room temperature. Half volume of acetone was evaporated off under reduced pressure. The mixture was cooled in an ice bath, and the resulting precipitates were filtered and washed with 30 ml of cold acetone to give 15.2 g of 5,6-O-isopropylidene-L-ascorbic acid. Then mother liquor was concentrated to give 3.8 g of 5,6-O-isopropylidene-L-ascorbic acid.

Workup

  1. stirringthe mixture was stirred for 1 hr at room temperature
  2. customHalf volume of acetone was evaporated off under reduced pressure
  3. temperatureThe mixture was cooled in an ice bath
  4. customthe resulting precipitates
  5. filtrationwere filtered
  6. washwashed with 30 ml of cold acetone

Sources & evidence

ORD record
ord-5411a013a5b8443f8dcf39d965b75631
Source dataset
uspto-grants-1986_01
Patent number
US04567282

Reaction notes

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