HCID 12786220, compound → HCID 12786221, compound

HRID 1389624Notes

Reaction equation

HRID 1389624 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][C@@H:13]1[CH2:17][CH2:16][CH2:15][C@H:14]1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1>C(Cl)Cl.CCOCC>[F:26][C:25]([F:27])([F:28])[C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][CH:14]1[CH2:15][CH2:16][CH2:17][C:13]1=[O:12]

Participants

5

Reactant 2

HCID 12786220HCID 12786220, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 12786221HCID 12786221, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 327.43 g of pyridinium chlorochromate in one liter of methylene chloride is added 220 g of trans-1-hydroxy-2-(3-trifluoromethylphenoxy)cyclopentane in 500 ml of methylene chloride. The mixture is stirred for 2 hours 15 minutes. Another 50 g of the oxidizing agent is added and the mixture is stirred for 41/2 hours. The mixture is diluted with ether and decanted from a black residue which is washed with more ether. The combined solutions are filtered through silica gel. The solvent is removed. The residue is dissolved in ether and again filtered through silica-gel. The solvent is removed and the residue is distilled (bp 113°-116° C., 1.5 mm) to give 188 g of 2-(3-trifluoromethylphenoxy)cyclopentanone.

Workup

  1. additionAnother 50 g of the oxidizing agent is added
  2. stirringthe mixture is stirred for 41/2 hours
  3. customdecanted from a black residue which
  4. washis washed with more ether
  5. filtrationThe combined solutions are filtered through silica gel
  6. customThe solvent is removed
  7. dissolutionThe residue is dissolved in ether
  8. filtrationagain filtered through silica-gel
  9. customThe solvent is removed
  10. distillationthe residue is distilled (bp 113°-116° C., 1.5 mm)

Sources & evidence

ORD record
ord-38cd10f1308c41f3b04f76787b8e0346
Source dataset
uspto-grants-1981_01
Patent number
US04245121

Reaction notes

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