Chloroform → HCID 13650571, compound

HRID 1194860Notes

Reaction equation

HRID 1194860 reaction equation
[CH2:1]([C:4]1[C:17]([OH:18])=[C:16]([CH3:19])[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>[F:20][C:9]1[C:8]2[C:7](=[O:21])[C:6]3[CH:5]=[C:4]4[CH2:1][CH:2]([C:37]([OH:38])=[O:40])[O:18][C:17]4=[C:16]([CH3:19])[C:15]=3[O:14][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 15617021HCID 15617021, compound

Product 1

HCID 13650571HCID 13650571, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-allyl-8-fluoro-3-hydroxy-4-methyl-9-oxo-9H-xanthene (9.0 g), m-chloroperbenzoic acid (8.0 g) and chloroform (1,000 ml) was stirred at room temperature for 5 hours and left to stand overnight. To the mixture, potassium carbonate (20 g) and water (500 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 (1,000 ml) and to the stirred solution, a mixture of chromium trioxide (21 g), water (120 ml) and concentrated sulfuric acid (36 g) was added dropwise at room temperature. After leaving it to stand 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 5.0 g of 6-fluoro-2,3-dihydro-11-methyl-5-oxo-5H-furo[3,2-b]xanthene-2-carboxylic acid. m.p. 292°-295° C. This compound produced a mass spectrum having a molecular ion peak at m/e 314.

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 (1,000 ml) and to the stirred solution
  7. additiona mixture of chromium trioxide (21 g), water (120 ml) and concentrated sulfuric acid (36 g)
  8. additionwas added dropwise at room temperature
  9. customAfter leaving it
  10. waitto stand overnight
  11. filtrationthe mixture was filtered
  12. customthe filtrate was evaporated to dryness under vacuum
  13. additionAfter addition of water
  14. filtrationthe solid crystal was recovered by filtration
  15. washwashed with water
  16. customdried
  17. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-333fe7740d4a4190b74670b5ae9328f8
Source dataset
uspto-grants-1989_03
Patent number
US04816479

Reaction notes

Loading…