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

HRID 412410Notes

Reaction equation

HRID 412410 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-dimethoxypropane (50 mL, 0.392 mmol). The mixture was refluxed at 100° C. for 2 hours and evaporated in vacuo. The residue was dissolved in diethyl ether (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-di-methyl-5-oxo-[1,3]dioxolan-4-yl)acetic acid as a solid.

Workup

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

Sources & evidence

ORD record
ord-818ec3ed3f4349688dd2ce1320aae51e
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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