Ethanol → ethyl (2S)-2-phenylpropanoate

HRID 59702Notes

Reaction equation

HRID 59702 reaction equation
[C:1]1([C@H:7]([CH3:11])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].[CH2:17](O)[CH3:18]>S(=O)(=O)(O)O>[C:1]1([C@H:7]([CH3:11])[C:8]([O:10][CH2:17][CH3:18])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 27246222-Phenylpropionic acid, (+)-

Product 1

HCID 7204861ethyl (2S)-2-phenylpropanoateYield 84%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution consisting of (S)-2-phenylpropanoic acid (1.0 g, 6.7 mmol, from Chem-Impex) in ethanol (30 mL) was added concentrated sulfuric acid (4 drops). The reaction mixture was stirred at reflux overnight in a vessel equipped with a Dean-Stark condenser. To the mixture was added solid sodium bicarbonate and the resulting mixture was filtered and concentrated under vacuum to afford the title compound (1.0 g, 84%) as a colorless oil; TLC Rf 0.5 (solvent system: 15:85:1 v/v/v ethyl acetate-heptane-acetic acid). The product was carried directly onto the next step without further purification.

Workup

  1. temperatureat reflux overnight in a vessel
  2. customequipped with a Dean-Stark condenser
  3. filtrationthe resulting mixture was filtered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e0ff38599c6e43f3a16cd9a5d255ed9d
Source dataset
uspto-grants-2016_09
Patent number
US09440919B2

Reaction notes

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