HCID 13343700, compound → HCID 13343701, compound

HRID 1154596Notes

Reaction equation

HRID 1154596 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[Cl:14][C:15]1[C:25]([C:26](=[O:34])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])=[CH:24][C:18]2[CH2:19][CH:20]([CH2:22][OH:23])[O:21][C:17]=2[C:16]=1[Cl:35]>CC(C)=O>[Cl:14][C:15]1[C:25]([C:26](=[O:34])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])=[CH:24][C:18]2[CH2:19][CH:20]([C:22]([OH:3])=[O:23])[O:21][C:17]=2[C:16]=1[Cl:35]

Participants

4

Reactant 2

HCID 13343700HCID 13343700, compoundHCID 131709961Jones' reagent

Product 1

HCID 13343701HCID 13343701, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones reagent [J. Chem. Soc., 2555 (1953)] (84 ml.) was added dropwise to a stirred, cooled solution of 6,7-dichloro-2,3-dihydro-5-(2-fluorobenzoyl)-2-hydroxymethylbenzofuran (43 g., 0.126 mole) in acetone (700 ml.) at such a rate that the internal temperature did not exceed 25° C. The resultant mixture was stirred for 18 hours at 25° C. The insoluble chromium salts were separated by decantation and washed with acetone. The washings were combined with the filtrate, and the resultant solution was concentrated to 1/5 the original volume and then poured into H2O. This mixture was extracted with methylene chloride and the organic extract was washed several times with aqueous NaCl. The methylene chloride solution was then extracted with 0.5N KOH. Upon standing the aqueous extract deposited the potassium carboxylate salt as a crystalline solid. The solid was dissolved in warm water, acidified with 6N HCl and the resulting solution extracted with ethyl acetate. Drying and evaporation furnished 38 g. of carboxylic acid, m.p. 180°-181° C. This material was used without additional purification for the next step.

Workup

  1. customdid not exceed 25° C
  2. customThe insoluble chromium salts were separated by decantation
  3. washwashed with acetone
  4. concentrationthe resultant solution was concentrated to 1/5 the original volume
  5. additionpoured into H2O
  6. extractionThis mixture was extracted with methylene chloride
  7. extractionthe organic extract
  8. washwas washed several times with aqueous NaCl
  9. extractionThe methylene chloride solution was then extracted with 0.5N KOH
  10. extractionaqueous extract
  11. dissolutionThe solid was dissolved in warm water
  12. extractionthe resulting solution extracted with ethyl acetate
  13. customDrying
  14. customevaporation
  15. customfurnished 38 g
  16. customThis material was used without additional purification for the next step

Sources & evidence

ORD record
ord-837fc663f7d24ec281ce5762790e12e8
Source dataset
uspto-grants-1984_12
Patent number
US04490384

Reaction notes

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