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

HRID 1154347Notes

Reaction equation

HRID 1154347 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]>O1CCOCC1>[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

4

Reactant 2

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

Product 1

HCID 130032262-Oxooctyl-p-ethoxybenzene sulfonateYield 59%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1.0 g quantity of 1-diazo-2-octanone is dissolved in 30 ml of dioxane, and 2.0 g of p-ethyoxybenzenesulfonic 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. distillationThe reaction mixture is distilled in a vacuum
  2. customto remove the solvent
  3. extractionthe residue is extracted with 50 ml of ether
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe dried product is distilled in a vacuum
  7. customto remove the solvent
  8. customobtain an oily product, which
  9. customis purified by column chromatography (silica gel, developer solvent chloroform)

Sources & evidence

ORD record
ord-b2185fd7dd794cb0afb812d2b21a39dd
Source dataset
uspto-grants-1984_12
Patent number
US04489091

Reaction notes

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