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

HRID 394617Notes

Reaction equation

HRID 394617 reaction equation
C(Cl)(=O)C.[O:5]=[C:6]1[O:12][C@H:11]([C@H:13]([CH2:15][OH:16])[OH:14])[C:9]([OH:10])=[C:7]1[OH:8].[CH3:17][C:18]([CH3:20])=O>>[CH3:17][C:18]1([CH3:20])[O:14][CH:13]([CH:11]2[O:12][C:6](=[O:5])[C:7]([OH:8])=[C:9]2[OH:10])[CH2:15][O:16]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 6367Acetyl chlorideHCID 54670067L-Ascorbic Acid

Product 1

HCID 546765085-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxy-2(5H)-furanoneYield 77%

Conditions

Temperature
32.5 °C

Procedure

5,6-O-isopropylidene-L-ascorbic acid was synthesized by the addition of acetyl chloride (124.9 mL) to a slurry of L-ascorbic acid USP (1000 g) in acetone (4.5 L). The mixture was stirred vigorously at 35-30° C. After two hours, the crystalline product separated. The crystals were collected by filtration, washed with cold acetone, and dried in a vacuum desciccator over potassium hydroxide pellets. The product, produced in 77% yield, consisted of needle-shaped crystals with a melting point of 217-223° C.

Workup

  1. customthe crystalline product separated
  2. filtrationThe crystals were collected by filtration
  3. washwashed with cold acetone
  4. dry with materialdried in a vacuum desciccator over potassium hydroxide pellets
  5. customThe product, produced in 77% yield

Sources & evidence

ORD record
ord-f001b44cc63c4991a0b339e264d0f5da
Source dataset
uspto-grants-2003_08
Patent number
US06602906B1

Reaction notes

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