Tert-butyl 2-(4-nitrophenoxy)acetate → Tert-butyl 2-(4-aminophenoxy)acetate

HRID 1682641Notes

Reaction equation

HRID 1682641 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 22061043Tert-butyl 2-(4-nitrophenoxy)acetate

Product 1

HCID 22060435Tert-butyl 2-(4-aminophenoxy)acetateYield 99%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

t-Butyl 4-nitrophenoxyacetate (19.3 g, 76.0 mmol) was dissolved in ethanol (100 ml) and 10% palladium-carbon (1.0 g) was added. The mixture was stirred at room temperature for 18 hours under a hydrogen atmosphere. The reaction mixture was filtrated and low boiling matters were distilled away from the filtrate under reduced pressure to give 16.8 g of t-butyl 4-aminophenoxyacetate as a pale-brown solid (99%).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. distillationlow boiling matters were distilled away from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-0c01652966d34f33a7cb94579742947f
Source dataset
uspto-grants-1997_06
Patent number
US05635527

Reaction notes

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