Toluene → HCID 13307780, compound

HRID 2109377Notes

Reaction equation

HRID 2109377 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:22]=[CH:21][C:16]([C:17](=O)[CH2:18]Br)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:11])[O:10][CH2:18][C:17]=2[C:16]2[CH:21]=[CH:22][C:13]([Cl:12])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 15880(4-Chlorophenyl)acetic acidHCID 68303p-Chlorophenacyl bromide

Product 1

HCID 13307780HCID 13307780, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

In acetonitrile (10 ml), a mixture of 4-chlorophenylacetic acid (1.70 g), 4-chlorophenacyl bromide (2.33 g) and potassium carbonate (5.53 g) was heated at reflux while stirring for 2 hours. Toluene and water were added to the reaction mixture, and the thus-precipitated crystals were filtered and purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/5), thereby giving 1.37 g of 3,4-bis(4-chlorophenyl)-2(5H)-furanone.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. filtrationthe thus-precipitated crystals were filtered
  4. custompurified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-857e420dc7844b758dd9d0feb9cc95a4
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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