Phenylmethylsulfonyl Fluoride → Cinnamoylbenzene

HRID 2379304Notes

Reaction equation

HRID 2379304 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([CH2:13]S(F)(=O)=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:18](Br)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20]>C(#N)C.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>[C:21]1([C:19](=[O:20])[CH:18]=[CH:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 4784Phenylmethylsulfonyl FluorideHCID 6259Phenacyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 7189CinnamoylbenzeneYield 152.9%

Reagents, catalysts & solvents 2

HCID 26541Dibenzo-18-crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

A catalytic amount (about 500 mg) of dibenzo-18-crown-6-ether and 68 g of anhydrous powdered potassium carbonate were added to a solution of 18.4 g phenylmethane-sulphonyl fluoride and 10.0 g of phenacyl bromide in 100 ml of acetonitrile at room temperature, while stirring. The mixture was then stirred under reflux for 10 hours. The reaction mixture was allowed to cool down to room temperature and was then concentrated by stripping off the solvent under reduced pressure. The residue was chromatographed over a silica gel column using toluene as the eluent. The eluate was evaporated. In this manner, 16.0 g of 1,3-di-phenyl-prop-2-en-1-one were obtained in the form of a solid substance of melting point 56° C.

Workup

  1. stirringThe mixture was then stirred
  2. temperatureunder reflux for 10 hours
  3. concentrationwas then concentrated
  4. customThe residue was chromatographed over a silica gel column
  5. customThe eluate was evaporated

Sources & evidence

ORD record
ord-79a638eb825e4ec999e90300678d1c91
Source dataset
uspto-grants-1994_11
Patent number
US05360935

Reaction notes

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