Ethyl Acetate → 3-Methyl-4-phenoxyaniline

HRID 1264032Notes

Reaction equation

HRID 1264032 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:15]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OCC)(=O)C>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[NH2:15]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 186166912-Methyl-4-nitro-1-phenoxybenzene

Product 1

HCID 155504883-Methyl-4-phenoxyanilineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 3-methyl-4-phenoxynitrobenzene (2) (548 g, 2.39 moles, 1.0 eq.) in methanol (5 L) was added 10% Pd/C (100 g, 50% wet, 46.98 mmol, 0.02 eq.). Then the reaction mixture was stirred under a hydrogen atmosphere (60-80 psi) for 15-16 hours at room temperature in a 2 gallon Parr hydrogenator. The progress of the reaction was monitored by TLC (50% ethyl acetate in hexanes, sm Rf=0.69, pr Rf=0.47, UV visible). Then the reaction mixture was filtered through Celite, and the solid was washed with excess methanol. The filtrate was concentrated under reduced pressure to give 3-methyl-4-phenoxyaniline as a pale brown viscous liquid (451.0 g, 95%). The 3-methyl-4-phenoxyaniline was found to be pure by 1H and 13C NMR spectra, and used as such in the next reaction

Workup

  1. filtrationThen the reaction mixture was filtered through Celite
  2. washthe solid was washed with excess methanol
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7a6dd9e4fe67489d897a24cfbeb46f4b
Source dataset
uspto-grants-2003_04
Patent number
US06541481B2

Reaction notes

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