Methanol → (3,3-Diphenyl-2-propenyl)-phenyl sulfone

HRID 1706053Notes

Reaction equation

HRID 1706053 reaction equation
[C:1]1([S:7]([O-:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].C(=O)([O-])[O-].[Na+].[Na+].CO.Br[CH2:20][CH:21]=[C:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[C:23]1([C:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:21][CH2:20][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 2723840Benzenesulfinic acid, sodium saltHCID 123465451,1'-(3-Bromoprop-1-ene-1,1-diyl)dibenzene

Product 1

HCID 20336784(3,3-Diphenyl-2-propenyl)-phenyl sulfoneYield 81.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.5 gm of sodium phenyl sulfinate and 1.5 gm of sodium carbonate were introduced into 80 cc of methanol. Then 25.6 gm of 1-bromo-3,3-diphenyl-2-propene were added to the reaction mixture under an atmosphere of nitrogen and at room temperature which was then agitated for 1 hour and 30 minutes. Next, the reaction mixture was poured into cold water and extracted with methylene chloride. The methylene chloride extracts were combined, washed with water, dried and concentrated to dryness. The residue was partly crystallized. The precipitate formed was isolated by vacuum filtering and dried to obtain 25.48 gm of (3,3-diphenyl-2-propenyl)-phenyl sulfone having a melting point of 104° C. A sample of this product, recrystallised from isopropyl ether, had a melting point of 106° C.

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. customThe residue was partly crystallized
  6. customThe precipitate formed
  7. customwas isolated by vacuum
  8. filtrationfiltering
  9. customdried

Sources & evidence

ORD record
ord-31f69094cfa347c4aee21468283c0e07
Source dataset
uspto-grants-1980_06
Patent number
US04206140

Reaction notes

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