Phenol → HCID 19970183, compound

HRID 974977Notes

Reaction equation

HRID 974977 reaction equation
[C:1]([C:3]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:4][CH:5]1[CH2:10][CH2:9][N:8](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:7][CH2:6]1)#[N:2].C1(O)C=CC=CC=1.[OH-].[Na+]>Br>[C:1]([C:3]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)#[N:2]

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 19970192HCID 19970192, compound

Product 1

HCID 19970183HCID 19970183, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 4-(2-cyano-2,2-diphenylethyl)-1-(4-methylphenylsulphonyl)piperidine (20 g, 45 mmol--see Preparation 14) and phenol (20 g) in 48% aqueous hydrobromic acid (200 ml) was heated under reflux for 2 hours, basified with 2M aqueous sodium hydroxide (100 g) cautiously with ice-cooling and extracted into dichloromethane. The organic layer was dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-10% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (10.0 g, 77%) as a colourless powder which was characterised by its 1H-NMR spectrum.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooling
  4. extractionextracted into dichloromethane
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by chromatography on silica
  8. customevaporated

Sources & evidence

ORD record
ord-29381b6b1345466d9134cee2ec1c008c
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

Loading…