Chloroform → HCID 13650579, compound

HRID 543420Notes

Reaction equation

HRID 543420 reaction equation
[CH2:1]([C:4]1[C:17]2[O:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:18])[C:8]=2[CH:7]=[C:6]([Cl:19])[C:5]=1[OH:20])[CH:2]=C.ClC1C=CC=C(C(OO)=O)C=1.C(Cl)(Cl)Cl.[C:36](=[O:39])([O-])[O-:37].[K+].[K+]>O>[Cl:19][C:6]1[C:5]2[O:20][CH:2]([C:36]([OH:37])=[O:39])[CH2:1][C:4]=2[C:17]2[O:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9](=[O:18])[C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 15617026HCID 15617026, compound

Product 1

HCID 13650579HCID 13650579, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-allyl-2-chloro-3-hydroxy-9-oxo-9H-xanthene (2.9 g), m-chloroperbenzoic acid (3.5 g) and chloroform (300 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 obtained 4-chloro-1,2-dihydro-2-hydroxymethyl-6-oxo-6H-furo[2,3-c]xanthene was dissolved in acetone (300 ml) and, to the stirred solution, a mixture of chromium trioxide (3.3 g), water (17 ml) and concentrated sulfuric acid (5 g) was added dropwise at room temperature. After standing overnight, to the mixture was added isopropanol (10 ml) and the resulting mixture was filtered and the filtrate was evaporated to dryness under vacuum. After adding water, the solid crystal was recovered by filtration, washed with water and dried. Recrystallization from ethanol gave 1.7 g of 4-chloro-1,2-dihydro-6-oxo-6H-furo[2,3-c]xanthene-2-carboxylic acid. m.p. 292°-295° C. This compound showed a mass spectrum having a molecular ion peak at m/e 316.

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 obtained 4-chloro-1,2-dihydro-2-hydroxymethyl-6-oxo-6H-furo[2,3-c]xanthene was dissolved in acetone (300 ml) and, to the stirred solution
  7. additiona mixture of chromium trioxide (3.3 g), water (17 ml) and concentrated sulfuric acid (5 g)
  8. additionwas added dropwise at room temperature
  9. waitAfter standing overnight, to the mixture
  10. additionwas added isopropanol (10 ml)
  11. filtrationthe resulting mixture was filtered
  12. customthe filtrate was evaporated to dryness under vacuum
  13. additionAfter adding water
  14. filtrationthe solid crystal was recovered by filtration
  15. washwashed with water
  16. customdried
  17. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-6b5e9fa467d24254ab5716425005e1a4
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

Loading…