Carbon Dioxide → HCID 15180802, compound

HRID 729112Notes

Reaction equation

HRID 729112 reaction equation
[C:1]1([C:7]2([C:27]([F:30])([F:29])[F:28])[C:20]3[CH:19]=[C:18](C(O)=O)[CH:17]=[CH:16][C:15]=3[O:14][C:13]3[C:8]2=[CH:9][C:10](C(O)=O)=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)=O>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[C:1]1([C:7]2([C:27]([F:30])([F:28])[F:29])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[O:14][C:15]3[C:20]2=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 280Carbon DioxideHCID 151808199-Phenyl-9-(trifluoromethyl)-9H-xanthene-2,7-dicarboxylic acid

Product 1

HCID 15180802HCID 15180802, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

A 6 g sample of 9-phenyl-9-trifluoromethylxanthene-2,7-dicarboxylic acid (XX) was stirred and refluxed in 100 ml quinoline along with 11 g of copper powder, the emanating gas being measured by a wet-test meter. The theoretical amount of CO2 was evolved in two hours. The reaction mixture was cooled, filtered through a bed of Celite into 800 ml of water,acidified with 100 ml of concentrated hydrochloric acid, and left standing overnight. The supernantant liquid was decanted, and the residue was takenup in methylene chloride, and filtered through a bed of alumina. The solvent was stripped, the residue was stirred with methanol, and was filtered, yielding 3.1 g (66%) of a white solid. It was recrystallized from methanol; m.p. 89-90°. The IR spectrum was sharp with no OH orCO bands. The NMR spectrum was confirmatory, with the following peaks: d 7.42; m 7.3-7.4; d 7.19, td 6.96, d 6.87 in 2:5:2:2:2 ratio. The compound was analyzed by mass spectrometry which showed the parent ion at 326, along with other peaks, the strongest being at 257 (parent minus trifluoromethyl), and also at 249 (parent minus phenyl), and 199 (parent minus phenyl and minus difluorocarbene). The mass spectrum confirmed the molecular formula as C2H13F3O.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through a bed of Celite into 800 ml of water,acidified with 100 ml of concentrated hydrochloric acid
  3. waitleft
  4. customThe supernantant liquid was decanted
  5. filtrationfiltered through a bed of alumina
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-7049170689b14564906586ab331087ad
Source dataset
uspto-grants-1991_09
Patent number
US05051520

Reaction notes

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