Phenol → HCID 15093848, compound

HRID 1709865Notes

Reaction equation

HRID 1709865 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)([CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:13]2)[C:9]#[N:10])=[CH:4][CH:3]=1.C1(O)C=CC=CC=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)([CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]2)[C:9]#[N:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 15093851HCID 15093851, compound

Product 1

HCID 15093848HCID 15093848, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of α,α-bis(4-fluorophenyl)-1-[(4-methylphenyl)sulfonyl]-3-piperidinepropanenitrile (41.21 g, 0.0858 mole) and phenol (100 g, 1.06 mole) was heated at reflux for 2 hours. the reaction mixture was cooled to room temperature and made alkaline with ice and 50% sodium hydroxide. The aqueous layer was extracted with chloroform. The chloroform layer was back extracted with 5% sodium hydroxide. The organic layer was then dried over sodium sulfate and filtered and solvent was removed to give a dark brown oil. This oil was subjected to flash chromatography on silica gel using methanol for elution. Fractions of similar purity were combined and solvent removed. The oil obtained was dried in vacuo overnight at 80° C., to give 18.83 g (67.2% yield) of brown oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. extractionThe aqueous layer was extracted with chloroform
  4. extractionThe chloroform layer was back extracted with 5% sodium hydroxide
  5. dry with materialThe organic layer was then dried over sodium sulfate
  6. filtrationfiltered
  7. customsolvent was removed
  8. customto give a dark brown oil
  9. washfor elution
  10. customsolvent removed
  11. customThe oil obtained
  12. customwas dried in vacuo overnight at 80° C.

Sources & evidence

ORD record
ord-c1e78c77b11d4d2099121c0aa9a76c27
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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