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

HRID 1106463Notes

Reaction equation

HRID 1106463 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-8c1d08c867bf4819bdba1c388364f78e
Source dataset
uspto-grants-2000_05
Patent number
US06057316

Reaction notes

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