Isopropanol → Diisopropyl (S)-(-)-malate

HRID 843280Notes

Reaction equation

HRID 843280 reaction equation
[C:1]([OH:9])(=[O:8])[C@H:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].[C:10]1(C)[CH:15]=CC(S(O)(=O)=O)=C[CH:11]=1.[CH:21](O)([CH3:23])[CH3:22]>>[C:1]([O:9][CH:21]([CH3:23])[CH3:22])(=[O:8])[C@H:2]([CH2:4][C:5]([O:7][CH:10]([CH3:15])[CH3:11])=[O:6])[OH:3]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 6101p-Toluenesulfonic acidHCID 222656L-Malic Acid

Product 1

HCID 11333435Diisopropyl (S)-(-)-malate

Procedure

(S)-malic acid was dissolved in isopropanol and p-toluenesulphonic acid (cat) was added and stirred at room temperature for 24 h. The reaction mixture was concentrated and distilled to give (S)-diisopropyl malate as colorless liquid. The residual material in the distillation flask was dissolved in EtOH and processed as above. Distillation afforded additional diester, raising the total yield.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. distillationdistilled

Sources & evidence

ORD record
ord-b40b84d951c54a0092c8ce12e5f00cd7
Source dataset
uspto-grants-2002_04
Patent number
US06376683B1

Reaction notes

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