Water → Methyl 2-hydroxy-3-phenylpropanoate

HRID 1534327Notes

Reaction equation

HRID 1534327 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[C:13](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C)C=O>[CH3:13][O:10][C:9]([CH:8]([OH:12])[CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 4447183-Phenyllactic acid, (S)-

Product 1

HCID 518800Methyl 2-hydroxy-3-phenylpropanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-3-Phenyllactic acid (5 g, 30 mmol) was dissolved in 25 mL of dimethylformamide and cesium carbonate (9.94 g, 30.5 mmol) was added. After the evolution of gas ceased, methyl iodide (8.52 g, 60 mmol) was added and the mixture was stirred for 18 hours at room temperature. Water was then added and the mixture extracted with ethyl acetate. The organic phase was separated, washed with water, dried over magnesium sulfate, and the solvent removed in vacuo to give the title compound as a colorless oil (5.4 g, 100% yield).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-026448d248964d70b257d9a58cf0a579
Source dataset
uspto-grants-1992_02
Patent number
US05089471

Reaction notes

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