Methanol → 1,4-dimethyl (2R)-2-hydroxybutanedioate

HRID 412415Notes

Reaction equation

HRID 412415 reaction equation
[C:1](Cl)(=O)C.[C:5]([OH:13])(=O)[C@@H:6]([CH2:8][C:9]([OH:11])=[O:10])[OH:7].[CH3:14][OH:15]>>[CH3:14][O:15][C:5](=[O:13])[C@H:6]([OH:7])[CH2:8][C:9]([O:11][CH3:1])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 92824D-Malic acid

Product 1

HCID 110626971,4-dimethyl (2R)-2-hydroxybutanedioate

Procedure

To an ice cooled solution of methanol (250 mL) was added acetyl chloride (12.5 mL), and the solution was stirred for 1 hour at 0° C. (R)-Malic acid (20.0 g) was added, and the solution was stirred for 16 hours at room temperature. Solvent was removed by evaporation in vacuo leaving a quantitative yield of (R)-2-hydroxysuccinic acid dimethyl ester as an oil.

Workup

  1. additionwas added
  2. customSolvent was removed by evaporation in vacuo

Sources & evidence

ORD record
ord-030a80fe485642f4a5f37c05f3fa5b37
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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