m-Chloroperbenzoic acid → HCID 19877238, compound

HRID 2106990Notes

Reaction equation

HRID 2106990 reaction equation
[C:1]1([CH:7]2[S:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][C:9]3([O:13][CH2:12][CH2:11][O:10]3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)Cl>[C:1]1([CH:7]2[S:16](=[O:31])[CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][C:9]3([O:13][CH2:12][CH2:11][O:10]3)[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12530025HCID 12530025, compound

Product 1

HCID 19877238HCID 19877238, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

23.4 g of 7,9-diphenyl-1,4-dioxa-8-thiaspiro[4.5]-decane are dissolved in 50 ml of methylene chloride and the solution is cooled to -10°. A solution of 16.0 g of m-chloroperbenzoic acid in 200 ml of methylene chloride is added dropwise in the course of about 7 hours, it being ensured that the temperature does not exceed -5°. The reaction mixture is then stirred at 0° for 16 hours and filtered and the residue is washed with 100 ml of methylene chloride. The combined methylene chloride solutions are washed three times with 150 ml of water each time, dried over sodium sulfate and evaporated. The colourless residue is stirred with 100 ml of 2N sodium hydroxide solution for 1 hour, filtered off, washed neutral, dried and crystallized from toluene. 7,9-Diphenyl-1,4-dioxa-8-thiaspiro[4.5]-decane 8-oxide is obtained as colourless crystals of melting point 230°-32°.

Workup

  1. temperaturethe solution is cooled to -10°
  2. customdoes not exceed -5°
  3. filtrationfiltered
  4. washthe residue is washed with 100 ml of methylene chloride
  5. washThe combined methylene chloride solutions are washed three times with 150 ml of water each time
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. stirringThe colourless residue is stirred with 100 ml of 2N sodium hydroxide solution for 1 hour
  9. filtrationfiltered off
  10. washwashed neutral
  11. customdried
  12. customcrystallized from toluene

Sources & evidence

ORD record
ord-d88ab8eff0b2485da87e1c28b806e09b
Source dataset
uspto-grants-1990_06
Patent number
US04933271

Reaction notes

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