Water → (S)-methyl 2-hydroxy-3-phenylpropanoate

HRID 611741Notes

Reaction equation

HRID 611741 reaction equation
[OH:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].O.[C:14]1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO>[OH:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:14])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4447183-Phenyllactic acid, (S)-HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of commercially available (S)-2-hydroxy-3-phenylpropionic acid (5.0 g, 30.1 mmol) and p-toluenesulfonic acid hydrate (1g) in methanol (125 mL) was refluxed with removal of water using 3A molecular sieves for 17 h. The solution was concentrated and dissolved in ether. The ether solution was washed with saturated sodium bicarbonate, brine and concentrated to provide the title compound as a white solid (5.32 g, 98%): NMR (CDCl3): δ 7.36-7.20 (m, 5H), 4.47 (ddd, J=5, 6, 7 Hz, 1H), 3.78 (s, 3H), 3.14 (dd, J=5, 14 Hz, 1H), 2.97 (dd, J=7, 14 Hz), 2.69 (d, J=6 Hz, 1H).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved in ether
  3. washThe ether solution was washed with saturated sodium bicarbonate, brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-190ec31dee234d999cd12da27342c0fe
Source dataset
uspto-grants-1999_12
Patent number
US06001867

Reaction notes

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