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

HRID 1069218Notes

Reaction equation

HRID 1069218 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 561.6%

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 (1 g) 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); δ7.36-7.20 (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-ff06c50958c04561984e1e4f45440828
Source dataset
uspto-grants-2001_06
Patent number
US06251936B1

Reaction notes

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