Potassium Persulfate → HCID 13732929, compound

HRID 1731824Notes

Reaction equation

HRID 1731824 reaction equation
S(OOS([O-])(=O)=O)([O-])(=O)=[O:2].[K+].[K+].[Br:13][C:14]1[CH:15]=[CH:16][C:17]2[O:27][C:20]3([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:19][C:18]=2[CH:28]=1>C(#N)C.O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]2[O:27][C:20]3([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:19](=[O:2])[C:18]=2[CH:28]=1

Participants

5

Reactant 2

HCID 24412Potassium Persulfate2×HCID 13732927HCID 13732927, compound

Product 1

HCID 13732929HCID 13732929, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 17.57 g of potassium persulfate, 5.19 g of cupric sulfate and 100 ml of distilled water was added a solution of 9.13 g of 5-bromo-spiro[benzofuran-2(3H),1'-cycloheptane] in 100 ml of acetonitrile. The mixture was stirred and heated to reflux; after 1.5 hours, GC showed only 6% unreacted starting material. Another 3.51 g of potassium persulfate was added and the mixture was refluxed for another hour and thereafter cooled to room temperature. The mixture was diluted with water (1.0 liter) and extracted with ether (1×500 ml, 2×250 ml). The combined ether extracts were washed with water (250 ml) and saturated sodium chloride solution (250 ml), dried overnight over anhydrous sodium sulfate, filtered and concentrated in vacuo to a gum weighing 7.63 g. This material was taken up in 100 ml of hexane and gravity-filtered to remove insoluble material, and the flask, filter paper and insoluble material were rinsed with another 100 ml of hexane. The hexane filtrate was concentrated in vacuo to an oil weighing 5.84 g. Vacuum distillation of this material afforded 2.76 g of viscous distillate, b.p. 135°-140° C. @ 0.15 mm.

Workup

  1. temperatureheated to reflux
  2. temperaturethe mixture was refluxed for another hour
  3. extractionextracted with ether (1×500 ml, 2×250 ml)
  4. washThe combined ether extracts were washed with water (250 ml) and saturated sodium chloride solution (250 ml)
  5. dry with materialdried overnight over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a gum
  8. filtrationgravity-filtered
  9. customto remove insoluble material
  10. filtrationthe flask, filter paper and insoluble material
  11. washwere rinsed with another 100 ml of hexane
  12. concentrationThe hexane filtrate was concentrated in vacuo to an oil
  13. distillationVacuum distillation of this material
  14. customafforded 2.76 g of viscous distillate, b.p. 135°-140° C.

Sources & evidence

ORD record
ord-34fc1c6f90974e03b52b0f68591ef836
Source dataset
uspto-grants-1986_11
Patent number
US04623657

Reaction notes

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