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

HRID 1910323Notes

Reaction equation

HRID 1910323 reaction equation
[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].O1CCOC1.CO[C:17](OC)([CH3:19])[CH3:18]>C1(C)C=CC=CC=1>[CH3:18][C:17]1([CH3:19])[O:3][CH:2]([CH2:4][C:5]([OH:7])=[O:6])[C:1](=[O:9])[O:8]1

Participants

5

Reactant 3

HCID 525Malic AcidHCID 64952,2-DimethoxypropaneHCID 125861,3-Dioxolane

Product 1

HCID 3578642-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Marketed DL-malic acid (with the 4 reference on the above schema) is protected in the dioxolane form in toluene reflux, in the presence of 2,2-dimethoxypropane. The reaction is quantitative. The obtained product (with the 5 reference in the above schema) is directly engaged in the following step.

Sources & evidence

ORD record
ord-aacc42d5197a4e5f98fac2d99752d22f
Source dataset
uspto-grants-2013_12
Patent number
US08603498B2

Reaction notes

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