2-Nitro-4-octylphenol → Phenol, 2-amino-4-octyl-

HRID 2300699Notes

Reaction equation

HRID 2300699 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:7]=[CH:6][C:5]=1[OH:18])([O-])=O>C(O)(=O)C.O.[Fe]>[NH2:1][C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:7]=[CH:6][C:5]=1[OH:18]

Participants

5

Reactant 1

HCID 186735512-Nitro-4-octylphenol

Product 1

HCID 87767Phenol, 2-amino-4-octyl-Yield 67%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To 95.4 mg(0.38 mmole) of 2-nitro-4-octylphenol in 2 ml of 1:1 glacial acetic acid and water mixture at 85-90° C. was added 0.35 gm of activated iron in three portions over a 15 min period. The reaction was allowed to proceed at the same temperature for 45 min. The reaction mixture was diluted then with 5 ml of water and extracted with 20 ml ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was flash chromatographed over silica gel using 30% ethyl acetate in hexane to yield 56 mg of 2-amino-4-octyl phenol, Structure (I-2), in 67% yield.

Workup

  1. additionThe reaction mixture was diluted
  2. extractionwith 5 ml of water and extracted with 20 ml ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated by rotary evaporation
  5. customchromatographed over silica gel using 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a6829e2b2d5e4ff28205ab5513ce3585
Source dataset
uspto-grants-2002_12
Patent number
US06498191B2

Reaction notes

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