p-Toluenesulfonic acid → 2,4-Dimethyl-6-tert-butylphenol

HRID 972084Notes

Reaction equation

HRID 972084 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[C:10]1([CH3:20])[CH:15]=CC(S(O)(=O)=O)=C[CH:11]=1.CC(=C)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:10]([CH3:20])([CH3:15])[CH3:11])[C:3]=1[OH:9]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 77712,4-DimethylphenolHCID 8255Isobutylene

Product 1

HCID 158842,4-Dimethyl-6-tert-butylphenolYield 2,443.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 1 liter flask equipped with a condenser, over-head stirrer, and gas inlet tube was added 2,4-dimethylphenol (200 g, 1.64 m.), toluene (400 ml), and p-toluenesulfonic acid (10 g). After heating this solution to reflux, isobutylene was added continuously for 14 hrs. Upon cooling, the solution was washed twice with water (400 ml), dried (MgSO4), and the solvent evaporated to afford a dark brown liquid. GC confirmed that this liquid was about 72% product. Distillation afforded 253 g (86.6%) of clear product which was shown to be 97% pure by GC.

Workup

  1. customTo a 1 liter flask equipped with a condenser, over-head stirrer, and gas inlet tube
  2. temperatureAfter heating this solution
  3. temperatureto reflux
  4. temperatureUpon cooling
  5. washthe solution was washed twice with water (400 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated
  8. customto afford a dark brown liquid
  9. distillationDistillation

Sources & evidence

ORD record
ord-9176f10901fa4680be16313bc4c3bfdd
Source dataset
uspto-grants-1979_07
Patent number
US04163008

Reaction notes

Loading…