Phenol → HCID 20218012, compound

HRID 236094Notes

Reaction equation

HRID 236094 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([CH:11]2[CH2:16][CH2:15][CH2:14][N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C1(O)C=CC=CC=1.[OH-].[Na+]>Br>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([CH:11]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 13607951HCID 13607951, compound

Product 1

HCID 20218012HCID 20218012, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 13.79 g (0.033 mole) of 3-[(3-chlorophenyl)sulfonyl]-1-[(4-methylphenyl)sulfonyl]piperidine and excess phenol in 300 ml of 48% hydrobromic acid was refluxed for 11/2 hr and then was poured over ice. The aqueous mixture was made basic with 50% sodium hydroxide and extracted with methylene chloride. The methylene chloride extract was dried over magnesium sulfate and the solvent was evaporated in vacuo to give an oil, the free base of the title compound. A solution of the oil in methanol was treated with excess ethereal hydrogen chloride, ether was added to give the hydrochloric acid salt which was recrystallized from methanol-ether to give 8.03 g (81.5%) white crystals, m.p. 179°-181° C.

Workup

  1. temperaturewas refluxed for 11/2 hr
  2. additionwas poured over ice
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. dry with materialwas dried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customto give an oil

Sources & evidence

ORD record
ord-033f8b9bf8064512ba61614ffb0c3e72
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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