Sulfuric Acid → 4-Butylphenol

HRID 2082634Notes

Reaction equation

HRID 2082634 reaction equation
N([O-])=O.[Na+].[CH2:5]([C:9]1[CH:15]=[CH:14][C:12](N)=[CH:11][CH:10]=1)[CH2:6][CH2:7][CH3:8].S(=O)(=O)(O)[OH:17].N(O)=O>O>[CH3:8][CH2:7][CH2:6][CH2:5][C:9]1[CH:15]=[CH:14][C:12]([OH:17])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 76944-ButylanilineHCID 24529Nitrous AcidHCID 23668193Sodium Nitrite

Product 1

HCID 154204-ButylphenolYield 73.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A cold solution of sodium nitrite (28.95g, 0.419m) in water (90ml) was added in drops to a mixture of 4-n-butylaniline (60g, 0.402m), concentrated sulfuric acid (135g) and water (300ml) at 0°-5° C with stirring. After completion of addition the excess nitrous acid was tested with potassium iodide starch paper, and destroyed by the addition of urea. The resulting cold diazonium salt solution was slowly added to a boiling solution of water (210ml), sulfuric acid (375g) and anhydrous sodium sulfate (285g). The resulting reaction mixture was steam distilled. The distillate was collected until it became clear and saturated by adding sodium chloride. The resulting solution was extracted with ether and the combined ether extract were dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was vacuum distilled to yield 4-n-butylphenol (44g, 73.3%), bp 106° C at 4.6 mm.

Workup

  1. customdestroyed by the addition of urea
  2. additionThe resulting cold diazonium salt solution was slowly added to a boiling solution of water (210ml), sulfuric acid (375g) and anhydrous sodium sulfate (285g)
  3. customThe resulting reaction mixture
  4. distillationdistilled
  5. distillationThe distillate was collected until it
  6. additionsaturated by adding sodium chloride
  7. extractionThe resulting solution was extracted with ether
  8. extractionthe combined ether extract
  9. dry with materialwere dried over anhydrous sodium sulfate
  10. customThe solvent was evaporated
  11. distillationdistilled

Sources & evidence

ORD record
ord-930151d80a314e928519ec0bd9b1f463
Source dataset
uspto-grants-1978_04
Patent number
US04082428

Reaction notes

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