2,2-Dimethoxypropane → 2-((4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

HRID 967609Notes

Reaction equation

HRID 967609 reaction equation
[CH2:1]([C:7]([OH:9])=[O:8])[C@@H:2]([OH:6])[C:3]([OH:5])=[O:4].CO[C:12](OC)([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[CH3:13][C:12]1([CH3:14])[O:6][C@H:2]([CH2:1][C:7]([OH:9])=[O:8])[C:3](=[O:5])[O:4]1

Participants

4

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 92824D-Malic acid

Product 1

HCID 108449602-((4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acidYield 22,997.801%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of D-(+)-malic acid (15.0 g, 0.1119 mol) in dry toluene (150 mL) was added 2,2-dimethyoxypropane (50 mL, 0.392 mmol). The mixture was refluxed at 100° C. for 2 hours and evaporated in vacuo. The residue was dissolved in diethylether (150 ml) and subjected to flash column chromatography using diethyl ether as eluent (200 mL). The pure fractions were pooled and evaporated in vacuo and the residue was stirred in n-hexane. The precipitate was collected, washed with n-hexane and dried to afford 15.7 g (81%) of (R)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)acetic acid as a solid.

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in diethylether (150 ml)
  3. customevaporated in vacuo
  4. customThe precipitate was collected
  5. washwashed with n-hexane
  6. customdried

Sources & evidence

ORD record
ord-8d1b3d7cd5b7407d9f5b332b51b301a2
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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