Sulfuric Acid → 1-(2-Methylphenyl)-1-phenyl-1-propene

HRID 1614807Notes

Reaction equation

HRID 1614807 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(O)[CH2:9][CH3:10].C(O)(C)C.S(=O)(=O)(O)O>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:9][CH3:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 212663251-(2-Methylphenyl)-1-phenyl-1-propanol

Product 1

HCID 544424051-(2-Methylphenyl)-1-phenyl-1-propeneYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2-Methylphenyl)-1-phenyl-1-propanol (10.4 g, 46 mmol) was dissolved into isopropanol (100 ml) and a 4 N sulphuric acid solution (50 ml) was added. The reaction mixture was heated at reflux temperature for 18 h and cooled to room temperature. Water (300 ml) was added and the mixture was extracted with dichloromethane (2×200 ml). The combined organic extracts was washed with a diluted sodium bicarbonate solution, dried over sodium sulphate and the solvent evaporated in vacuo to give 9.0 g (91% of 1-(2-methylphenyl)-1-phenyl-1-propene.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 18 h
  3. extractionthe mixture was extracted with dichloromethane (2×200 ml)
  4. washThe combined organic extracts was washed with a diluted sodium bicarbonate solution
  5. dry with materialdried over sodium sulphate
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-e54fd5ddeb8147aa8dadb173b362f25c
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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