Benzenepropanoic acid → Methyl 3-phenylpropionate

HRID 652363Notes

Reaction equation

HRID 652363 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:12]O>>[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 107Benzenepropanoic acidHCID 887Methanol

Product 1

HCID 7643Methyl 3-phenylpropionateYield 96.3%

Procedure

A mixture of 3-phenylpropionic acid (118.2 g, 788 mmol) sulfuric acid (5.9 g), and 100 mL of methanol was heated to reflux overnight. TLC analysis indicated the absence of starting material and the reaction was concentrated in vacuo. The residue was dissolved in 200 mL of ethyl ether, washed with sodium bicarbonate (100 mL), dried over magnesium sulfate, filtered and concentrated to give 124.4 g (96.3%) of the ester as a tan oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationthe reaction was concentrated in vacuo
  4. dissolutionThe residue was dissolved in 200 mL of ethyl ether
  5. washwashed with sodium bicarbonate (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-89aaf64e23854e17bec8a5abff95f799
Source dataset
uspto-grants-1987_06
Patent number
US04670462

Reaction notes

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