Water → Methyl 2-hydroxy-3-phenylpropanoate

HRID 1110927Notes

Reaction equation

HRID 1110927 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-153c98764ab841459af79b88076699ac
Source dataset
uspto-grants-1990_12
Patent number
US04977141

Reaction notes

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