Benzenepropanoic acid → Methyl 3-phenylpropionate

HRID 2419366Notes

Reaction equation

HRID 2419366 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.S(=O)(=O)(O)O.[CH3:17]O>>[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH3:17])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 107Benzenepropanoic acidHCID 887MethanolHCID 1118Sulfuric Acid

Product 1

HCID 7643Methyl 3-phenylpropionate

Procedure

A mixture of 3-phenylpropionic acid (50g.), methanol (250ml.) and concentrated sulphuric acid (12ml.) was heated under reflux for 12 hours, and then the excess of methanol was evaporated under reduced pressure. The residue was added to saturated aqueous sodium bicarbonate solution (100ml.) containing ice (400g.) and the pH adjusted to 9 by the addition of more sodium bicarbonate solution. The mixture was extracted with ether (5 × 100ml.), and the extracts combined, washed with brine (2 × 50ml.), dried and evaporated to give methyl 3-phenylpropionate as an oil with a peak at 1740 cm-1 in its I.R. spectrum.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. customthe excess of methanol was evaporated under reduced pressure
  4. additionThe residue was added to saturated aqueous sodium bicarbonate solution (100ml.)
  5. additioncontaining ice (400g.)
  6. additionthe pH adjusted to 9 by the addition of more sodium bicarbonate solution
  7. extractionThe mixture was extracted with ether (5 × 100ml.)
  8. washwashed with brine (2 × 50ml.)
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-7a0253d6fb414bd29ecc45b1673990a6
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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