Acetic Acid → HCID 87572695, compound

HRID 2262388Notes

Reaction equation

HRID 2262388 reaction equation
[I-].[C:2]([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([S+:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]3[CH:23]=[CH:24][CH:25]=[CH:26][C:15]2=3)=[CH:10][CH:9]=1)(=[O:4])[CH3:3].[OH-].C[N+](C)(C)C.C(O)(=O)C>CO.C(Cl)(Cl)Cl.C([O-])(=O)C.[Ag+]>[C:2]([O-:5])(=[O:4])[CH3:3].[OH:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([S+:14]2[C:15]3[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]2=3)=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 60966Tetramethylammonium hydroxideHCID 87123706HCID 87123706, compound

Product 1

HCID 87572695HCID 87572695, compoundYield 154.8%

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 2-phenylethyl acetate 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. The crystals precipitated are recovered by filtration to obtain 11.1 g of 5-[4-(2-acetoxyethyl)phenyl]dibenzothiophenium iodide. The obtained 11.1 g of 5-[4-(2-acetoxyethyl)phenyl]-dibenzothiophenium iodide is dissolved in 200 ml of methanol, and 10.7 g of a 20% aqueous solution of tetramethylammonium hydroxide is added to the reaction solution. After stirring the reaction solution at room temperature for 2 hours, 10 ml of acetic acid is added and the reaction solution is further stirred at room temperature for 30 minutes. Further, 3.9 g of silver acetate is added to the reaction solution and 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/acetonitrile (10/1), whereby 6.6 g of 5-[4-(2-hydroxyethyl)phenyl]dibenzo-thiophenium acetate is obtained.

Workup

  1. stirringthe reaction solution is further stirred at room temperature for 30 minutes
  2. stirringstirred at room temperature for 1 hour
  3. filtrationAfter filtering the reaction solution
  4. distillationthe mother liquor is distilled off under reduced pressure
  5. customThe crystals obtained
  6. washwashed with water three times
  7. distillationAfter distilling off the chloroform under reduced pressure
  8. customthe reaction product is recrystallized with ethyl acetate/acetonitrile (10/1)

Sources & evidence

ORD record
ord-084601fc753947ee9b56260ae1aa72b0
Source dataset
uspto-grants-2010_12
Patent number
US07851130B2

Reaction notes

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