Tetramethylammonium hydroxide → HCID 87381192, compound

HRID 909987Notes

Reaction equation

HRID 909987 reaction equation
[I-].C([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)C.[OH-].C[N+](C)(C)C.[CH:33]([C:36]1[CH:41]=[CH:40][C:39]([S:42]([OH:45])(=[O:44])=[O:43])=[C:38]([CH:46]([CH3:48])[CH3:47])[C:37]=1C(C)C)([CH3:35])[CH3:34]>CO.C(Cl)(Cl)Cl.C([O-])(=O)C.[Ag+]>[CH:7]([C:40]1[CH:41]=[C:36]([CH:33]([CH3:35])[CH3:34])[CH:37]=[C:38]([CH:46]([CH3:47])[CH3:48])[C:39]=1[S:42]([O-:45])(=[O:44])=[O:43])([CH3:8])[CH3:6].[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 60966Tetramethylammonium hydroxideHCID 19107298HCID 19107298, compoundHCID 87123706HCID 87123706, compound

Product 1

HCID 87381192HCID 87381192, compoundYield 101.6%

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 further 10 ml of 2-phenylethyl acetate is 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. 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 solution. After stirring the solution at room temperature for 2 hours, 9.6 g of triisopropylbenzenesulfonic acid is aded and the reaction solution is further stirred at room temperature for 30 minutes. Silver acetate (3.9 g) is added to the reaction solution and stirred at room temperature for 1 hour. After filtering the reaction solution, the mother liquor is distilled under reduced pressure. The crystals obtained are dissolved in chloroform, and washed with water three times. After distilling off chloroform under reduced pressure, the reaction product is recrystallized with ethyl acetate/acetonitrile (5/1), whereby 7.0 g of 5-[4-(2-hydroxy-ethyl)phenyl]dibenzothiophenium 2,4,6-triisopropylbenzene-sulfonate 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 under reduced pressure
  5. customThe crystals obtained
  6. washwashed with water three times
  7. distillationAfter distilling off chloroform under reduced pressure
  8. customthe reaction product is recrystallized with ethyl acetate/acetonitrile (5/1)

Sources & evidence

ORD record
ord-f8399b2ac741420aa9b53b90c48c5636
Source dataset
uspto-grants-2011_09
Patent number
US08021819B2

Reaction notes

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