Acetic Acid → HCID 87571982, compound

HRID 2262387Notes

Reaction equation

HRID 2262387 reaction equation
[I-].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([S+:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11]3[CH:18]=[CH:19][CH:20]=[CH:21][C:10]2=3)=[CH:5][CH:4]=1.[C:22]([OH:25])(=[O:24])[CH3:23]>CO.C(Cl)(Cl)Cl.C([O-])(=O)C.[Ag+]>[C:22]([O-:25])(=[O:24])[CH3:23].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([S+:9]2[C:10]3[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]2=3)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 87572850HCID 87572850, compound

Product 1

HCID 87571982HCID 87571982, compound

Reagents, catalysts & solvents 3

HCID 11246Silver acetateCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

While cooling with ice, 10.0 g of dibenzothiophene-S-oxide synthesized in the above step (1) is added to 30 g of diphosphorus pentoxide/methanesulfonic acid (9/1), and 10 ml of toluene is further added thereto. The reaction solution is stirred at room temperature for 6 hours, and then poured into ice water. The obtained aqueous solution is filtered, and 23 g of potassium iodide is added thereto. The crystals precipitated are recovered by filtration to obtain 9.1 g of 5-(4-methylphenyl)dibenzothiophenium iodide. The obtained 9.1 g of 5-(4-methylphenyl)dibenzothiophenium iodide is dissolved in 200 ml of methanol, and 10 ml of acetic acid is added to the reaction solution. After stirring the reaction solution at room temperature for 30 minutes, 3.9 g of silver acetate is further added thereto, and the reaction solution is further stirred at room temperature for 1 hour. After filtering the reaction solution, the mother liquor is distilled off under reduced pressure. The crystals obtained are dissolved in chloroform, and washed with water three times. After distilling off the chloroform under reduced pressure, the reaction product is recrystallized with ethyl acetate, whereby 6.2 g of 5-(4-methylphenyl)dibenzothiophenium acetate is obtained.

Workup

  1. stirringthe reaction solution is further stirred at room temperature for 1 hour
  2. filtrationAfter filtering the reaction solution
  3. distillationthe mother liquor is distilled off under reduced pressure
  4. customThe crystals obtained
  5. washwashed with water three times
  6. distillationAfter distilling off the chloroform under reduced pressure
  7. customthe reaction product is recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-3c15230b009f4350abd64c4dd96a90ae
Source dataset
uspto-grants-2010_12
Patent number
US07851130B2

Reaction notes

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