Nitric Acid → 4-(1-Methylpropyl)-2-nitrophenol

HRID 1723007

Reaction equation

HRID 1723007 reaction equation
O.[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([CH2:4][CH3:5])[CH3:3].[N+:13]([O-])([OH:15])=[O:14]>CCOCC>[CH:2]([C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=1)([CH2:4][CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 74534-sec-Butylphenol

Product 1

HCID 190854-(1-Methylpropyl)-2-nitrophenol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 50 ml of water, 50 ml of ether and 10.0 g of 4-sec-butylphenol was added dropwise, 7.5 ml of 61% nitric acid was added dropwise while cooling with ice. After, the temperature of the mixture was raised to room temperature and the reaction was continued for 4 days. The reaction mixture was extracted with 300 ml of ethyl acetate, washed with a brine and dried with anhydrous sodium sulfate. The drying agent was filtered off and the solvent was distilled away. The residue was purified by subjecting to silica-gel column-chromatography [eluent:chloroform] to give 14.71 g of 4-sec-butyl-2-nitrophenol.

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooling with ice
  3. extractionThe reaction mixture was extracted with 300 ml of ethyl acetate
  4. washwashed with a brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. distillationthe solvent was distilled away
  8. customThe residue was purified

Sources & evidence

ORD record
ord-04bff3161a584e8d916e77a66dbd2775
Source dataset
uspto-grants-1989_08
Patent number
US04859661

Linked notes

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