4-ethoxybenzenesulfonic Acid → 2-Oxooctyl-p-ethoxybenzene sulfonate

HRID 648231Notes

Reaction equation

HRID 648231 reaction equation
[N+](=[CH:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[N-].[CH2:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([OH:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1)[CH3:13]>>[O:11]=[C:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][O:24][S:21]([C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:12][CH3:13])=[CH:20][CH:19]=1)(=[O:22])=[O:23]

Participants

3

Reactant 2

HCID 70130204-ethoxybenzenesulfonic AcidHCID 537252081-Diazo-2-octanone

Product 1

HCID 130032262-Oxooctyl-p-ethoxybenzene sulfonateYield 59%

Procedure

A 1.0 g quantity of 1-diazo-2-octanone is dissolved in 30 ml of dixoane, and 2.0 g of p-ethoxybenzenesulfonic acid is slowly added to the solution at room temperature. The mixture is stirred until no nitrogen is evolved. The reaction mixture is distilled in a vacuum to remove the solvent, and the residue is extracted with 50 ml of ether, washed with water and dried over anhydrous sodium sulfate. The dried product is distilled in a vacuum to remove the solvent and obtain an oily product, which is purified by column chromatography (silica gel, developer solvent chloroform), affording 1.26 g of 2-oxooctyl-p-ethoxybenzene sulfonate (Compound 46), m.p. 38° to 39° C. Yield 59.0%.

Workup

  1. additionis slowly added to the solution at room temperature
  2. distillationThe reaction mixture is distilled in a vacuum
  3. customto remove the solvent
  4. extractionthe residue is extracted with 50 ml of ether
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe dried product is distilled in a vacuum
  8. customto remove the solvent
  9. customobtain an oily product, which
  10. customis purified by column chromatography (silica gel, developer solvent chloroform)

Sources & evidence

ORD record
ord-ad36fde1397a475fa514be8426a5d9a1
Source dataset
uspto-grants-1983_10
Patent number
US04411911

Reaction notes

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