4-tert-Butylphenol → HCID 15225594, compound

HRID 1770127Notes

Reaction equation

HRID 1770127 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)C#N.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].[C:21](=[O:24])([O-])[O-:22].[K+].[K+].S([O-])(O)(=O)=O.[K+]>N1C=CC=CC=1>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([O:20][C:2]2[CH:9]=[C:8]([CH:7]=[CH:4][CH:3]=2)[C:21]([OH:22])=[O:24])=[CH:18][CH:19]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 73934-tert-ButylphenolHCID 11430Potassium CarbonateHCID 233813-BromobenzonitrileHCID 516920Potassium bisulfate

Product 1

HCID 15225594HCID 15225594, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-bromobenzonitrile (4.35 g, 23.9 mmol) and p-t-butylphenol (4.30 g, 28.7 mmol) in pyridine (45 ml) were added potassium carbonate (6.61 g, 47.8 mmol) and cupric oxide (3.42 g, 43 mmol), and the resultant mixture was refluxed for 46 hours. The reaction mixture was poured into saturated potassium hydrogensulfate solution and extracted with ethyl acetate. The organic layer was concentrated, and the residue was dissolved in ethylene glycol (20 ml), mixed with 2N potassium hydroxide solution (130 ml) and refluxed for 20 hours. The reaction mixture was poured into chilled water and extracted with diethyl ether under acidic conditions. The organic layer was dried and concentrated. The residue was chromatographed on a silica gel column to give the titled compound (3.46 g, yield 54%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. dissolutionthe residue was dissolved in ethylene glycol (20 ml)
  4. additionmixed with 2N potassium hydroxide solution (130 ml)
  5. temperaturerefluxed for 20 hours
  6. additionThe reaction mixture was poured
  7. temperatureinto chilled water
  8. extractionextracted with diethyl ether under acidic conditions
  9. customThe organic layer was dried
  10. concentrationconcentrated
  11. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-1222ec5818264b4799c8833871b84b14
Source dataset
uspto-grants-1995_01
Patent number
US05385917

Reaction notes

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