Ethanol → HCID 20295300, compound

HRID 1389759Notes

Reaction equation

HRID 1389759 reaction equation
F[B-](F)(F)F.[C:6]1([S+:12]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)C.[S:40]([C:44]1[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=1)([O-:43])(=[O:42])=[O:41].[K+]>O>[C:47]1([CH3:48])[CH:46]=[CH:45][C:44]([S:40]([O-:43])(=[O:41])=[O:42])=[CH:50][CH:49]=1.[CH2:13]([S+:12]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 20295297HCID 20295297, compoundHCID 23689124Potassium p-toluenesulfonate

Product 1

HCID 20295300HCID 20295300, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5.0 g diphenyl-n-octadecyl sulfonium tetrafluoroborate in 20 ml. of ethanol is added 20.0 g of potassiumtosylate dissolved in a mixture of 200 ml. ethanol and 10 ml. water. The reaction mixture is maintained at 80°-90° while being stirred vigorously for 2 hours. The reaction mixture is then cooled and evaporated i.v. to dryness. The residue is taken up in methylene chloride; the organic phase washed several times with water, dried over sodium sulphate, filtered and evaporated i.v. to dryness. The residue is chromatographed over silica gel three times using methylene chloride and increasing amounts of methanol to obtain n-octadecyldiphenylsulfonium p-toluenesulfonate.

Workup

  1. dissolutiondissolved in a mixture of 200 ml
  2. temperatureThe reaction mixture is maintained at 80°-90°
  3. temperatureThe reaction mixture is then cooled
  4. customevaporated i.v
  5. washthe organic phase washed several times with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated i.v
  9. customThe residue is chromatographed over silica gel three times
  10. temperatureincreasing amounts of methanol

Sources & evidence

ORD record
ord-e15781a0e52f4a7dac047e5643d7e3dd
Source dataset
uspto-grants-1981_01
Patent number
US04246259

Reaction notes

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