Methanol → 1,1-Diphenylethylene

HRID 1416100Notes

Reaction equation

HRID 1416100 reaction equation
CO.[C:3]1([CH3:13])[CH:8]=[CH:7][C:6](S(O)(=O)=O)=[CH:5][CH:4]=1>C1(C)C=CC=CC=1>[C:3]1([C:13]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH2:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 6101p-Toluenesulfonic acid

Product 1

HCID 107401,1-DiphenylethyleneYield 36,321.398%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into a 1-liter reaction flask were introduced 200.23 g of the crude carbinol, 400 ml of toluene, and 1 g of p-toluenesulfonic acid (PTSA). Azeotropic dehydration was conducted for 2 hours with toluene refluxing (94-116° C.). After cooling, this reaction mixture was washed with water, with 2% aqueous soda ash solution, and then with water, dried with magnesium sulfate, and concentrated to obtain 190.09 g of crude 1,1-diphenylethylene (9a; R1 =R2 =H). This crude 1,1-diphenylethylene (9a) was distilled with a Claisen flask equipped with a vigreux, giving 174.06 g of 1,1-diphenylethylene (9a). b.p., 103° C./1 mmHg

Workup

  1. customInto a 1-liter reaction flask
  2. temperatureAfter cooling
  3. washthis reaction mixture was washed with water, with 2% aqueous soda ash solution
  4. dry with materialwith water, dried with magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-feefe0f308d74e9a8b200c4500acb066
Source dataset
uspto-grants-1999_06
Patent number
US05910610

Reaction notes

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