Methane → 4-(4-Aminophenoxy)phenol

HRID 1655444Notes

Reaction equation

HRID 1655444 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C.C1COCC1.[H][H]>[Pt].C(OCC)(=O)C>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:16]=[CH:17][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 8028TetrahydrofuranHCID 1524504-(4-Nitrophenoxy)phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 152173634-(4-Aminophenoxy)phenolYield 96.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-Hydroxyphenoxy)-4-nitrobenzene X (8.93 g, 38.62 mmol), 0.5% platinum catalyst on activated charcoal (1.5 g), THF (100 mL), and ethyl acetate (20 mL) were charged into a 250 mL hydrogenation vessel. Hydrogenation was carried out under 60 psi of hydrogen at room temperature for 16 hr. The reaction mixture was filtered and the organic solvents were removed under reduced pressure at 40° C. to give 4-(4-aminophenoxy)phenol XI (8.10 g, 96.2% yield), mp 130°-4° C. The IR and 1H-NMR spectra agreed with the assigned structure.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe organic solvents were removed under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-79fa8365654d416986b231c4af5c4489
Source dataset
uspto-grants-1993_10
Patent number
US05250667

Reaction notes

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