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

HRID 2102213Notes

Reaction equation

HRID 2102213 reaction equation
[C:1]([OH:9])(=[O:8])[C@@H:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].CO[C:12](OC)([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[CH3:13][C:12]1([CH3:14])[O:3][C@H:2]([CH2:4][C:5]([OH:7])=[O:6])[C:1](=[O:9])[O:8]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 acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 25.05 g D-malic acid and 68.1 g 2,2-dimethoxypropane in 200 mL toluene was refluxed for 2 hours under nitrogen. The solvent was removed under reduced pressure to give the title compound as a white solid. 1H NMR (CDCl3, 500 MHz) δ 4.76 (dd, J=3.9 & 6.6 Hz, 1H), 3.02 (dd, J=3.9 & 17.2 Hz, 1H), 2.88 (dd, J=6.6 & 17.2 Hz, 1H), 1.64 (s, 3H), 1.59 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ba22a2cdc90a4c68b6d43678af9fab1c
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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