Hydrochloric Acid → HCID 86612198, compound

HRID 490049Notes

Reaction equation

HRID 490049 reaction equation
C([O:9][CH:10]([C:18]([F:21])([F:20])[F:19])[C:11]([F:17])([F:16])[S:12]([O-:15])(=[O:14])=[O:13])(=O)C1C=CC=CC=1.[C:22]1([S+:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[Na+].Cl>CO>[OH:9][CH:10]([C:18]([F:21])([F:19])[F:20])[C:11]([F:16])([F:17])[S:12]([O-:15])(=[O:14])=[O:13].[C:35]1([S+:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23118490Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-benzoyloxypropane-1-sulfonate

Product 1

HCID 86612198HCID 86612198, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 72 g of methanol was dissolved 34.4 g of triphenylsulfonium 2-benzoyloxy-1,1,3,3,3-pentafluoropropane-1-sulfonate synthesized in Synthesis Example 10. While the solution was stirred under ice cooling, 54.0 g of 5% sodium hydroxide solution was added dropwise at a temperature below 10° C. It was aged at the temperature for 4 hours. At a temperature below 10° C., 6.8 g of 12N hydrochloric acid was added to quench the reaction. The methanol was distilled off in vacuum, after which 270 g of dichloromethane was added to the residue. The organic layer was washed with 40 g of water three times. The organic layer was concentrated, after which 60 g of diethyl ether was added to the residue for crystallization. The crystals were filtered and dried, obtaining the target compound. White crystals, 24.3 g (yield 85%).

Workup

  1. customsynthesized in Synthesis Example 10
  2. customto quench
  3. customthe reaction
  4. distillationThe methanol was distilled off in vacuum
  5. additionafter which 270 g of dichloromethane was added to the residue
  6. washThe organic layer was washed with 40 g of water three times
  7. concentrationThe organic layer was concentrated
  8. additionafter which 60 g of diethyl ether was added to the residue for crystallization
  9. filtrationThe crystals were filtered
  10. customdried
  11. customobtaining the target compound

Sources & evidence

ORD record
ord-31ab757b50554bbdb508c3b6fbf1bf45
Source dataset
uspto-grants-2009_05
Patent number
US07527912B2

Reaction notes

Loading…