Hydrochloric Acid → Phenol, 2,6-bis(1,1-dimethylethyl)-4-nitroso-

HRID 597121

Reaction equation

HRID 597121 reaction equation
C(O)C.Cl.[C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:10]=1[OH:19])([CH3:8])([CH3:7])[CH3:6].[N:20]([O-])=[O:21].[Na+]>O>[N:20]([C:13]1[CH:14]=[C:9]([C:5]([CH3:8])([CH3:7])[CH3:6])[C:10]([OH:19])=[C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=1)=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 314052,6-Di-tert-butylphenolHCID 23668193Sodium Nitrite

Product 1

HCID 70383Phenol, 2,6-bis(1,1-dimethylethyl)-4-nitroso-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ethanol (75 ml) was cooled to 15° C and saturated with hydrogen chloride gas. This solution was diluted by addition of another 400 ml of ethanol. To this alcoholic solution was added 82.4 grams of 2,6-di-tert-butylphenol. After it was dissolved, a solution of 30.4 grams of sodium nitrite in 40 ml of water was added at 15°-20° C over a period of one hour with stirring. Stirring was continued for another two hours with the temperature allowed to rise to room temperature. The solution was diluted with 200 ml of water, and the product formed was collected by filtration and washed well with water. The filter cake was then slurried in 300 ml of petroleum ether, filtered, washed with another 100 ml of petroleum ether and dried in a vacuum oven at 70°-80° C to yield the desired intermediate 4-nitroso-2,6-di-tert-butylphenol, melting at 219° C.

Workup

  1. dissolutionAfter it was dissolved
  2. stirringStirring
  3. customto rise to room temperature
  4. customthe product formed
  5. filtrationwas collected by filtration
  6. washwashed well with water
  7. filtrationfiltered
  8. washwashed with another 100 ml of petroleum ether
  9. customdried in a vacuum oven at 70°-80° C

Sources & evidence

ORD record
ord-0fa31e1b27f3480587e8e1bb040bd9fc
Source dataset
uspto-grants-1977_03
Patent number
US04013621

Linked notes

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