4-Benzyl-2-nitrophenol → 2-Amino-4-benzylphenol

HRID 2075248Notes

Reaction equation

HRID 2075248 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([N+:15]([O-])=O)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CO>[NH2:15][C:10]1[CH:9]=[C:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][C:11]=1[OH:14]

Participants

4

Reactant 1

HCID 7863744-Benzyl-2-nitrophenol

Product 1

HCID 2650022-Amino-4-benzylphenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon, Pearlman, (50% wet) (2.3 g, 2.2 mmol) and 4-benzyl-2-nitrophenol (5.00 g, 22 mmol) were combined under nitrogen and diluted with 80 mL MeOH delivered via syringe. The vessel was pressurized to 40 psi and shaken in a Parr shaker for ˜24 h. The resulting material was flushed with nitrogen and filtered through Celite, rinsing with MeOH. The filtrate was concentrated in vacuo to give 2-amino-4-benzylphenol as a brown solid. MS (ESI) m/z: Calculated: 199.1; Observed: 200.0 (M++1).

Workup

  1. customdelivered via syringe
  2. customThe resulting material was flushed with nitrogen
  3. filtrationfiltered through Celite
  4. washrinsing with MeOH
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-25d6e736352f48ae9e15484aafbb5be7
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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