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

HRID 1109428Notes

Reaction equation

HRID 1109428 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([O:10][CH:11]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:12]([F:15])([F:14])[F:13])=[O:9])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH:11]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:12]([F:13])([F:14])[F:15])=[O:9])=[CH:22][CH:23]=1

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, then, the organic 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 1,1,1-trifluoro-2-octyl p-nitrobenzoate. 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 then the ethanol was distilled off under a reduced pressure to obtain 1.8 g of 1,1,1-trifluoro-2-octyl p-aminobenzoate 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-e0236ec1a72241ec837a225744ddc510
Source dataset
uspto-grants-1994_06
Patent number
US05320776

Reaction notes

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