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

HRID 1180662Notes

Reaction equation

HRID 1180662 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].S(=O)(=O)(O)O.[O:10]=[C:11]1[O:17][C@H:16]([C@H:18]([CH2:20]O)[OH:19])[C:14]([OH:15])=[C:12]1[OH:13]>>[CH3:1][C:2]1([CH3:4])[O:19][CH:18]([CH:16]2[O:17][C:11](=[O:10])[C:12]([OH:13])=[C:14]2[OH:15])[CH2:20][O:3]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 54670067L-Ascorbic Acid

Product 1

HCID 546765085-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxy-2(5H)-furanoneYield 115.4%

Procedure

With nitrogen substitution, 557.8 grams (9.6 moles) of acetone was cooled to −5 degrees C., 54.3 grams (0.2 moles) of 28% fuming sulfuric acid was dripped, and 176.1 grams (1.0 mole) of L-ascorbic acid was added. The mixture was then reacted at the temperature of the previous step for 17 hours, filtered and washed with cold acetone to obtain 249.5 grams of 5,6-O-isopropylidene-L-ascorbic acid (86.7% in purity) in the form of a wet cake.

Workup

  1. customThe mixture was then reacted at the temperature of the previous step for 17 hours
  2. filtrationfiltered
  3. washwashed with cold acetone

Sources & evidence

ORD record
ord-791e98c0e714494494edee84fc7b4241
Source dataset
uspto-grants-2007_10
Patent number
US07282597B2

Reaction notes

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