Phenol → 2,5-dimethyl-4-nitrosophenol

HRID 1645889Notes

Reaction equation

HRID 1645889 reaction equation
S(=O)(=O)(O)O.[C:6]1([OH:14])[C:7]([CH3:13])=[CH:8][CH:9]=[C:10]([CH3:12])[CH:11]=1.C1(O)C=CC=CC=1.[N:22]([O-])=[O:23].[Na+]>O.C(O)(=O)C>[N:22]([C:9]1[CH:8]=[C:7]([CH3:13])[C:6]([OH:14])=[CH:11][C:10]=1[CH3:12])=[O:23]

Participants

7

Reactant 4

HCID 996PhenolHCID 1118Sulfuric AcidHCID 72672,5-DimethylphenolHCID 23668193Sodium Nitrite

Product 1

HCID 2802082,5-dimethyl-4-nitrosophenol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

A solution of 20 mL of 36N sulfuric acid solution in 40 mL of water (60 mL of 12N sulfuric acid) is added to a mixture of 6I g (500 mmol) of 2,5-xylenol and 200 mL of glacial acetic acid. A homogeneous solution is produced initially, but on continued stirring some of the phenol crystallizes. A solution of 35 g (500 mmol) of sodium nitrite in 60 mL of water is added dropwise to the previous mixture over 60 minutes at 5° to 10° C. Stirring is continued for 10 to 15 minutes and the heterogeneous mixture is poured into 1 L of water. The reaction flask is rinsed with water and the solid nitroso derivative collected, washed with water, and dried to a moist cake.

Workup

  1. customA homogeneous solution is produced initially
  2. customcrystallizes
  3. washThe reaction flask is rinsed with water
  4. washthe solid nitroso derivative collected, washed with water
  5. customdried to a moist cake

Sources & evidence

ORD record
ord-92b6794391db4596916c946b24545686
Source dataset
uspto-grants-1993_01
Patent number
US05177106

Reaction notes

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