3,5-Dimethylphenol → 3,5-Dimethyl-4-nitrosophenol

HRID 1284955Notes

Reaction equation

HRID 1284955 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[N:10]([O-])=[O:11].[Na+]>C(O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[C:7]=1[N:10]=[O:11]

Participants

5

Reactant 2

HCID 79483,5-DimethylphenolHCID 23668193Sodium Nitrite

Product 1

HCID 2360193,5-Dimethyl-4-nitrosophenolYield 71.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

750 ml of concentrated HClare added to a solution of 3,5-dimethyl phenol (80.6 g) in 750 ml of 95% ethyl alcohol. The mixture is cooled to 0° C. in an ice/methanol bath. While maintaining the temperature of the reaction mixture below 5° C. a solution of NaNO2 (69.0 g) in 150 ml of H2O is added dropwise to the reaction mixture. The mixture is stirred at 0° C. for more than an hour and then poured into 9 liters of water. The aqueous mixture is filtered to give a yellow solid which is recrystallized from hot methanol and filtered to give 71.45 grams of a yellow solid, M.P. 180°-181° C. (dec).

Workup

  1. additionis added dropwise to the reaction mixture
  2. filtrationThe aqueous mixture is filtered
  3. customto give a yellow solid which
  4. customis recrystallized from hot methanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-8747f9542fbf467f9dfa62465296144d
Source dataset
uspto-grants-1986_01
Patent number
US04564640

Reaction notes

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