Ethanol → Ethyl 4-(4-aminophenyl)butanoate

HRID 1702674Notes

Reaction equation

HRID 1702674 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([O-])=O.[H][H].[CH2:18](O)[CH3:19]>[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:18][CH3:19])=[O:14])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 797114-(4-Nitrophenyl)butyric acidHCID 178418361HCID 178418361, compound

Product 1

HCID 10013251Ethyl 4-(4-aminophenyl)butanoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 10.0 g. of 4-(4-nitrophenyl)butyric acid in 150 ml. of ethanol containing 50 mg. of a 10% palladium on carbon catalyst is hydrogenated until the uptake of hydrogen ceases. After the system is purged with nitrogen and the solution is filtered through a celite pad, 3 ml. of boron trifluoride etherate is added and the solution is heated to reflux for 10 hours. Upon cooling and evaporation of the ethanol, a colorless residue is obtained. This product is recrystallized from ethanol-hexane and affords ethyl 4-(4-aminophenyl)butyrate.

Workup

  1. customAfter the system is purged with nitrogen
  2. filtrationthe solution is filtered through a celite pad, 3 ml
  3. additionof boron trifluoride etherate is added
  4. temperaturethe solution is heated
  5. temperatureto reflux for 10 hours
  6. temperatureUpon cooling
  7. customevaporation of the ethanol
  8. customa colorless residue is obtained
  9. customThis product is recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-c0bd9808e6a74addbea8ceb29d255201
Source dataset
uspto-grants-1982_09
Patent number
US04348399

Reaction notes

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