Sulfuric Acid → 1,1-Diphenyl-1-propene

HRID 1614802Notes

Reaction equation

HRID 1614802 reaction equation
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(O)[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C)C.S(=O)(=O)(O)O.C(CC(C)(C)C)(C)C>O>[C:1]1([C:7]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 109072,2,4-TrimethylpentaneHCID 2261491,1-Diphenylpropan-1-ol

Product 1

HCID 2382071,1-Diphenyl-1-propeneYield 49.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,1-diphenyl-1-propanol (64 g, 0.30 mol), isopropanol (300 ml) and a 5 N solution of sulphuric acid (150 ml) was heated at reflux temperature for 18 h. The reaction mixture was cooled, diluted with water (600 ml) and extracted with toluene (3×150 ml). The combined organic phases was dried over sodium sulphate and the solvent was evaporated in vacuo to give a solid residue which was trituated with iso-octane. The solid was collected by filtration to give 28.8 g (49%) of 1,1-diphenyl-1-propene.

Workup

  1. temperatureat reflux temperature for 18 h
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with toluene (3×150 ml)
  4. dry with materialThe combined organic phases was dried over sodium sulphate
  5. customthe solvent was evaporated in vacuo
  6. customto give a solid residue which
  7. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-856ab6b4a6ac4b4ea13c01cd505911e1
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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