Ethanol → HCID 20572291, compound

HRID 1577309Notes

Reaction equation

HRID 1577309 reaction equation
F[B-](F)(F)F.[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S+:17]([CH2:36][CH2:37][CH3:38])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])([O:8][CH2:9][CH3:10])=[O:7].C(O)C.[S:42]([C:46]1[CH:52]=[CH:51][C:49]([CH3:50])=[CH:48][CH:47]=1)([O-:45])(=[O:44])=[O:43].[K+].O>C(Cl)Cl>[C:49]1([CH3:50])[CH:48]=[CH:47][C:46]([S:42]([O-:45])(=[O:43])=[O:44])=[CH:52][CH:51]=1.[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S+:17]([CH2:36][CH2:37][CH3:38])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 962WaterHCID 12760768HCID 12760768, compoundHCID 23689124Potassium p-toluenesulfonate

Product 1

HCID 20572291HCID 20572291, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.0 g of o-carbethoxyphenyl-n-propyl-n-octadecylsulfonium tetrafluoroborate in 20 ml. of ethanol is added 20.0 g of potassium tosylate 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 filtered, and the filtrate then evaporated under vacuum to dryness to obtain a residue. The residue is taken up in methylene chloride; the organic phase washed several times with water, dried over sodium sulphate, filtered and evaporated under vacuum to dryness. The residue is chromatographed over silica gel three times using methylene chloride and increasing amounts of methanol to obtain the title product m.p. 65°-67°.

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. filtrationfiltered
  5. customthe filtrate then evaporated under vacuum to dryness
  6. customto obtain a residue
  7. washthe organic phase washed several times with water
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated under vacuum to dryness
  11. customThe residue is chromatographed over silica gel three times
  12. temperatureincreasing amounts of methanol

Sources & evidence

ORD record
ord-d9874629d29d482cb198e38ecbffd9c6
Source dataset
uspto-grants-1981_09
Patent number
US04287355

Reaction notes

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