p-Chlorobenzenesulfonic acid → HCID 13003243, compound

HRID 648232Notes

Reaction equation

HRID 648232 reaction equation
[N+](=[CH:3][C:4](=[O:14])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N-].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1>CCOCC>[O:14]=[C:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:3][O:25][S:22]([C:19]1[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][CH:20]=1)(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 7400p-Chlorobenzenesulfonic acidHCID 1959731-diazo-2-oxoundecane

Product 1

HCID 13003243HCID 13003243, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 1.2 g quantity of 1-diazo-2-undecanone is dissolved in 50 ml of ether, and 1.6 g of p-chlorobenzenesulfonic acid is slowly added to the solution at room temperature. The mixture is stirred until no nitrogen is evolved. The reaction mixture is washed with water, and the ethereal layer is dried over anhydrous sodium sulfate and distilled in a vacuum to remove the solvent. The residue is recrystallized from ether/petroleum ether to give 1.62 g of 2-oxoundecyl-p-chlorobenzene sulfonate (Compound 68), m.p. 51° to 51.5° C. Yield 75.3%.

Workup

  1. washThe reaction mixture is washed with water
  2. dry with materialthe ethereal layer is dried over anhydrous sodium sulfate
  3. distillationdistilled in a vacuum
  4. customto remove the solvent
  5. customThe residue is recrystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-ef46015a430b4b94a77928f68125ce5a
Source dataset
uspto-grants-1983_10
Patent number
US04411911

Reaction notes

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