Chloroform → HCID 13650574, compound

HRID 543419Notes

Reaction equation

HRID 543419 reaction equation
[CH2:1]([C:4]1[C:17]([OH:18])=[C:16]([Cl:19])[C:15]2[O:14][C:13]3[C:8](=[C:9]([F:20])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:21])[C:6]=2[CH:5]=1)[CH:2]=C.ClC1C=CC=C(C(OO)=O)C=1.C(Cl)(Cl)Cl.[C:37](=[O:40])([O-])[O-:38].[K+].[K+]>O>[Cl:19][C:16]1[C:15]2[O:14][C:13]3[CH:12]=[CH:11][CH:10]=[C:9]([F:20])[C:8]=3[C:7](=[O:21])[C:6]=2[CH:5]=[C:4]2[CH2:1][CH:2]([C:37]([OH:38])=[O:40])[O:18][C:17]=12

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 15617024HCID 15617024, compound

Product 1

HCID 13650574HCID 13650574, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-allyl-4-chloro-8-fluoro-3-hydroxy-9-oxo-9H-xanthene (2.8 g), m-chloroperbenzoic acid (4.7 g) and chloroform (100 ml) was stirred at room temperature for 5 hours and thereafter left to stand overnight. To the mixture, potassium carbonate (10 g) and water (200 ml) were added and the resulting mixture was extracted with chloroform. The chloroform layer was dried and the solvent was distilled off. The residue was dissolved in acetone (500 ml) and, to the stirred solution, a mixture of chromium trioxide (2.8 g), water (16 ml) and concentrated sulfuric acid (4.8 g) was added dropwise at room temperature. After standing overnight, the mixture was filtered and the filtrate was evaporated to dryness under vacuum. After addition of water, the solid crystal was recovered by filtration, washed with water and dried. Recrystallization from ethanol gave 1.0 g of 11-chloro-6-fluoro-2,3-dihydro-5-oxo-5H-furo[3,2-b]xanthene-2-carboxylic acid. m.p. 300° C. This compound showed a mass spectrum having a molecular ion peak at m/e 334.

Workup

  1. waitleft
  2. waitto stand overnight
  3. extractionthe resulting mixture was extracted with chloroform
  4. dry with materialThe chloroform layer was dried
  5. distillationthe solvent was distilled off
  6. dissolutionThe residue was dissolved in acetone (500 ml) and, to the stirred solution
  7. additiona mixture of chromium trioxide (2.8 g), water (16 ml) and concentrated sulfuric acid (4.8 g)
  8. additionwas added dropwise at room temperature
  9. waitAfter standing overnight
  10. filtrationthe mixture was filtered
  11. customthe filtrate was evaporated to dryness under vacuum
  12. additionAfter addition of water
  13. filtrationthe solid crystal was recovered by filtration
  14. washwashed with water
  15. customdried
  16. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-0a754499ebc94fe593faf32a8ca48934
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

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