Acetone → (S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

HRID 2415023Notes

Reaction equation

HRID 2415023 reaction equation
[CH3:1][O:2][C:3]([O:6][CH3:7])([CH3:5])[CH3:4].[OH2:8].[O-2:9].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3].C[C:27]([CH3:29])=[O:28]>>[CH3:4][C:3]1([CH3:5])[O:6][C@@H:7]([CH2:29][C:27]([OH:8])=[O:28])[C:1](=[O:9])[O:2]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 64952,2-DimethoxypropaneHCID 71586775Bentonite

Product 1

HCID 641720(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

Conditions

Temperature
5 °C

Procedure

(L)-Malic acid (200 g) was added to a mixture of acetone (800 mL) and 2,2-dimethoxypropane (342 mL) with stirring under nitrogen. Montmorillonite K-10 clay (5 g) was added to the solution and stirred for 17 hours, then the solution was filtered and reduced in volume to approximately 450 mL. The solution was cooled to 5° C., and the resultant crystals of the title compound filtered off (108 g, 42%). MP 108-109.5° C.

Workup

  1. stirringstirred for 17 hours
  2. filtrationthe solution was filtered
  3. filtrationthe resultant crystals of the title compound filtered off (108 g, 42%)

Sources & evidence

ORD record
ord-1fb5a16fc1244bb4a12487413758d3ea
Source dataset
uspto-grants-2004_11
Patent number
US06818622B2

Reaction notes

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