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

HRID 1278802Notes

Reaction equation

HRID 1278802 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); 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-d44eba2cf45c47d59814283289356b42
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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