Phosgene → HCID 70362464, compound

HRID 2072751Notes

Reaction equation

HRID 2072751 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C1(C2C=CC=CC=2)C=CC=CC=1.[CH3:17][C:18]1[CH:19]=[C:20]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([CH3:32])[CH:26]=2)[CH:21]=[CH:22][C:23]=1[CH3:24].[C:33](Cl)(Cl)=[O:34]>C(=S)=S>[CH3:31][C:28]1[C:33](=[O:34])[C:30]2[C:25](=[CH:26][C:27]=1[CH3:32])[C:20]1[C:21](=[CH:22][C:23]([CH3:24])=[C:18]([CH3:17])[CH:19]=1)[CH:29]=2

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 7095BiphenylHCID 210291,1'-Biphenyl, 3,3',4,4'-tetramethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 70362464HCID 70362464, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

35.6 g of anhydrous aluminium chloride are added in portions to a solution of 20 g of biphenyl according to (a) and 14 g of phosgene in 130 ml of carbon disulfide at -10° C. to 0° C. in the course of 2 hours. After stirring at room temperature for 15 hours, the mixture is refluxed for 2 hours, poured onto ice-water and extracted with 1.5 l of chloroform. The residue from the organic phase (22.9 g) is separated by column chromatography on silica gel. Elution with methylene chloride/toluene=13:7 gives 9.8 g of 1,2,6,7-tetramethyl-fluorenone (Rf value 0.62) and 10.04 g of 2,3,6,7-tetramethyl-fluorenone (Rf value 0.41).

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. additionpoured onto ice-water
  3. extractionextracted with 1.5 l of chloroform
  4. customThe residue from the organic phase (22.9 g) is separated by column chromatography on silica gel
  5. washElution with methylene chloride/toluene=13:7

Sources & evidence

ORD record
ord-4859f6cea4bf4817bd313bd4762dd513
Source dataset
uspto-grants-1990_04
Patent number
US04914182

Reaction notes

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