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

HRID 1931901Notes

Reaction equation

HRID 1931901 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-:13])=[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-:13])=[O:12].[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

7

Reactant 3

HCID 313Hydrochloric AcidHCID 79483,5-DimethylphenolHCID 23668193Sodium Nitrite

Product 2

HCID 1384663,5-Dimethyl-4-nitrophenolHCID 2360193,5-Dimethyl-4-nitrosophenolYield 143.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

[3,5-Dimethyl-4-nitrophenol was synthesized by the reference procedures (U.S. Pat. No. 4,564,640)] 750 ml of Concentrated hydrochloric acid was added to a solution of 3,5-dimethylphenol (80.6 g) in 750 ml of 95% ethanol. The mixture was 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 water was added dropwise to the reaction mixture. The mixture was stirred at 0° C. for more than an hour and then poured into 9 liters of water. The aqueous mixture was filtered to give a yellow solid which was recrystallized from hot methanol and filtered to give 71.45 g of 3,5-dimethyl-4-nitrosophenol as a yellow solid. Mp. 180-181° C.

Workup

  1. temperatureWhile maintaining the temperature of the reaction mixture below 5° C.
  2. filtrationThe aqueous mixture was filtered
  3. customto give a yellow solid which
  4. customwas recrystallized from hot methanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-351be53f9c6f4d8d841ff848abc0b407
Source dataset
uspto-grants-2012_05
Patent number
US08188314B2

Reaction notes

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