1,1,1-Trifluoro-2-octyl p-nitrobenzoate → 1,1,1-Trifluoro-2-octyl p-aminobenzoate

HRID 1109431Notes

Reaction equation

HRID 1109431 reaction equation
[F:1][C:2]([F:23])([F:22])[CH:3]([O:10][C:11](=[O:21])[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>C(O)C.[Pd]>[F:1][C:2]([F:22])([F:23])[CH:3]([O:10][C:11](=[O:21])[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 1

HCID 152195301,1,1-Trifluoro-2-octyl p-nitrobenzoate

Product 1

HCID 152195311,1,1-Trifluoro-2-octyl p-aminobenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The reaction liquid was poured into water, and extracted with methylene chloride. The methylene chloride layer was washed with a diluted hydrochloric acid and water in this order. The organic layer thus recovered was distilled under a reduced pressure to remove the solvent, and subjected to purification by a silica gel chromatography (n-hexane:ethyl acetate=10:2) to obtain 1.9 g of p-nitrobenzoic acid 1,1,1-trifluoro-2-octyl ester. The ester was dissolved in 30 ml of ethanol, to which 0.19 g of 5% Pd-C catalyst was added. After the solution was stirred overnight under hydrogen atmosphere, the Pd-C catalyst was separated by filtration, and the ethanol was distilled off under a reduced pressure to obtain 1.8 g of p-aminobenzoic acid 1,1,1-trifluoro-2-octyl ester which was the desired compound of the reaction 1).

Workup

  1. additionwas added
  2. customthe Pd-C catalyst was separated by filtration
  3. distillationthe ethanol was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-bcb78b293cda45cdbd2c89a5ecab4bae
Source dataset
uspto-grants-1994_06
Patent number
US05320776

Reaction notes

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