Boron trifluoride etherate → Ethyl 3-(4-aminophenyl)propanoate

HRID 1702668Notes

Reaction equation

HRID 1702668 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.B(F)(F)F.[CH3:17][CH2:18]OCC.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([O:10][CH2:17][CH3:18])=[O:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 754513-(4-Aminophenyl)propionic acid

Product 1

HCID 10442595Ethyl 3-(4-aminophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10.0 g. p-aminohydrocinnamic acid in 100 ml. of absolute ethanol containing 16 ml. of boron trifluoride etherate is heated to reflux for 48 hours. The solution is then cooled, poured into 5% aqueous sodium carbonate, and extracted with methylene chloride. Evaporation of the organic extracts yields ethyl p-aminohydrocinnamate.

Workup

  1. temperatureto reflux for 48 hours
  2. temperatureThe solution is then cooled
  3. extractionextracted with methylene chloride
  4. customEvaporation of the organic extracts

Sources & evidence

ORD record
ord-4b067c01df694480809cfd06d7e2d4da
Source dataset
uspto-grants-1982_09
Patent number
US04348399

Reaction notes

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