Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 19774074, compound

HRID 1613557Notes

Reaction equation

HRID 1613557 reaction equation
[C:1]1([S:7][CH2:8][C:9]2([C:12]3([CH3:17])OCC[O:13]3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CC(C)=O.C1(C)C=CC=CC=1>[C:12]([C:9]1([CH2:8][S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][CH2:10]1)(=[O:13])[CH3:17]

Participants

6

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 19774077HCID 19774077, compound

Product 1

HCID 19774074HCID 19774074, compoundYield 1,520.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Conditions

Temperature
4 °C

Procedure

A mixture of 5 (7.23 g, 2.94 mmol) and pyridinium p-toluenesulfonate (0.74 g, 2.94 mmol) in acetone (150 mL) was stirred in a cold room at 4° C. for 5 days. The mixture was neutralized with sodium bicarbonate solution, and diluted with toluene. After evaporation of acetone, the residue was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, and dried over sodium sulfate. Filtration and concentration gave 9.22 g of an oily material, which was purified by column chromatography (silica gel 60 g, 4-16% ethyl acetate in n-hexane) to give 6.16 g (quantitative) of 6, as a pale yellow oil.

Workup

  1. customAfter evaporation of acetone
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-ba0aa26d3272495e962989d344f1e7bc
Source dataset
uspto-grants-1993_03
Patent number
US05194431

Reaction notes

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