Acetic Acid → Methyl 2-(4-aminophenyl)-2-methylpropanoate

HRID 889960Notes

Reaction equation

HRID 889960 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([CH3:15])([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)[CH3:5].C(O)(=O)C>C1COCC1.[Zn]>[CH3:1][O:2][C:3](=[O:16])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[CH:10][CH:11]=1)([CH3:15])[CH3:5]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 11299024HCID 11299024, compound

Product 1

HCID 584407Methyl 2-(4-aminophenyl)-2-methylpropanoate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-2-(4-nitro-phenyl)-propionic acid methyl ester (2.1 g) was dissolved in THF (70 ml) and acetic acid (5 ml) and Zn (10 g) were added. The mixture was stirred for 1 h and filtered through Celite®. The filtrate was rinsed with EtOAc and the organics were evaporated to a residue which was purified on silica gel chromatography (40%EtOAc/hexanes) to provide the desired compound as a yellow oil. M+H 194.

Workup

  1. filtrationfiltered through Celite®
  2. washThe filtrate was rinsed with EtOAc
  3. customthe organics were evaporated to a residue which
  4. customwas purified on silica gel chromatography (40%EtOAc/hexanes)

Sources & evidence

ORD record
ord-d9d3825fbd00458b90cdc271b2ebfeb1
Source dataset
uspto-grants-2006_02
Patent number
US06995162B2

Reaction notes

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