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

HRID 1956609Notes

Reaction equation

HRID 1956609 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].C(Cl)(=O)C.[CH3:17][C:18]([CH3:20])=O>>[CH3:17][C:18]1([CH3:20])[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

4

Reactant 3

HCID 180AcetoneHCID 6367Acetyl chlorideHCID 54670067L-Ascorbic Acid2×

Product 1

HCID 546765085-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxy-2(5H)-furanoneYield 79%

Procedure

Initially, 5,6-O-isopropylidene-L-ascorbic acid (IAA) was prepared by adding L-ascorbic acid (100 gm, 0.57 mole) into a three-necked 1-liter flask equipped with a mechanical stirrer and a thermometer. The L-ascorbic acid was followed by acetone (450 ml) and acetyl chloride (12.5 ml), and the whole mixture was stirred vigorously at 30°-40° C. for 2 hours.

Workup

  1. customequipped with a mechanical stirrer

Sources & evidence

ORD record
ord-60c35b08dae84a3f8d639364316b35f5
Source dataset
uspto-grants-1998_07
Patent number
US05780504

Reaction notes

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