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

HRID 2098987Notes

Reaction equation

HRID 2098987 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-221d7290e5c645c6ac17e0206b9ea75c
Source dataset
uspto-grants-2009_08
Patent number
US07569211B2

Reaction notes

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