Nitric Acid → 4-Benzyl-2-nitrophenol

HRID 2075247Notes

Reaction equation

HRID 2075247 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:15]([O-])([OH:17])=[O:16]>CC(O)=O>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 75634-Benzylphenol

Product 1

HCID 7863744-Benzyl-2-nitrophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 4-benzylphenol (10.0 g, 54.3 mmol) in 300 mL AcOH at ambient temperature was added slowly dropwise a solution of nitric acid, red fuming (2.28 mL, 54.3 mmol) in 100 mL AcOH over 1-2 h. The reaction was allowed to stir for 3 h, poured onto ice, and the resulting solid was collected by filtration, rinsing with water to give 4-benzyl-2-nitrophenol as a yellow solid. MS (ESI) m/z: Calculated: 229.1; Observed: 227.8 (M++1).

Workup

  1. additionpoured onto ice
  2. filtrationthe resulting solid was collected by filtration
  3. washrinsing with water

Sources & evidence

ORD record
ord-03f297eb96c94b0a89cb388f4db30d06
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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