Hydrochloric Acid → 3,5-Dimethyl-4-nitrosophenol

HRID 246846Notes

Reaction equation

HRID 246846 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[C:7]([CH3:9])[CH:8]=1.[N:11]([O-])=[O:12].[Na+]>C(O)C.O>[CH3:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[C:7]([CH3:9])[C:8]=1[N:11]=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 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 HCl are 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. temperatureWhile maintaining the temperature of the reaction mixture below 5° C.
  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-d6e6e8558e2a40d6908c8ce59898e7a1
Source dataset
uspto-grants-1987_11
Patent number
US04704401

Reaction notes

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