Pyridine → HCID 86735161, compound

HRID 973137Notes

Reaction equation

HRID 973137 reaction equation
N1C=CC=CC=1.[C:7]1([OH:15])[C:8](=[CH:10][C:11](=[CH:13][CH:14]=1)[OH:12])[CH3:9].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)(Cl)Cl>[CH3:16][S:17]([CH:9]([S:17]([CH3:16])(=[O:19])=[O:18])[C:8]1[C:7]([OH:15])=[CH:14][CH:13]=[C:11]([OH:12])[CH:10]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7253MethylhydroquinoneHCID 31297Methanesulfonyl chloride

Product 1

HCID 86735161HCID 86735161, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 500 ml. of pyridine was dissolved 124 g. of toluhydroquinone and then 170 ml. of methanesulfonyl chloride was added dropwise to the solution while stirring at a temperature below 25° C. Thereafter, the mixture was further stirred for one hour at room temperature. After the reaction was over, 500 ml. of chloroform was added to the reaction mixture and the resultant mixture was washed several times with water, then with 10% hydrochloric acid and finally once with water. The chloroform layer formed was recovered and dried over anhydrous sodium sulfate. After filtering, the solvent was distilled off from the filtrate and the residue formed was recrystallized from methanol to provide 230 g. of the desired compound of a melting point of 80° to 82° C.

Workup

  1. stirringThereafter, the mixture was further stirred for one hour at room temperature
  2. washthe resultant mixture was washed several times with water
  3. customThe chloroform layer formed
  4. customwas recovered
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtering
  7. distillationthe solvent was distilled off from the filtrate
  8. customthe residue formed
  9. customwas recrystallized from methanol
  10. customto provide 230 g

Sources & evidence

ORD record
ord-5660de898f174212b31efce5938ab3e3
Source dataset
uspto-grants-1977_10
Patent number
US04055428

Reaction notes

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