Hydrochloric Acid → Methyl 2-hydroxy-3-phenylpropanoate

HRID 1357221Notes

Reaction equation

HRID 1357221 reaction equation
Cl.[OH:2][CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5].[C:14]([O-])(O)=O.[Na+]>CO>[CH3:14][O:5][C:4](=[O:6])[CH:3]([OH:2])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3848(+-)-3-Phenyllactic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 518800Methyl 2-hydroxy-3-phenylpropanoateYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen chloride was bubbled for 15 minutes into a solution of 2-hydroxy-3-phenyl-propionic acid (10.0 g, 60 mmol) in 100 mL of methanol at room temperature. The vessel was sealed and then stirred overnight at room temperature. The reaction was made basic by the addition of 5% NaHCO3 and then concentrated under reduced pressure to remove the methanol. The residue was diluted with water and extracted with ethyl acetate. The organic layer was extracted with saturated NaCl, dried (MgSO4) and the solvent removed under reduced pressure to give 2-hydroxy-3-phenyl-propionic acid methyl ester (9.7 g, 90%) as a yellow oil, MS m/z 180 [M]+.

Workup

  1. customThe vessel was sealed
  2. concentrationconcentrated under reduced pressure
  3. customto remove the methanol
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. extractionThe organic layer was extracted with saturated NaCl
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-76a2948ee8aa4ba2affa4f26b3a4b8c4
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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