Water → HCID 23432392, compound

HRID 1012364Notes

Reaction equation

HRID 1012364 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br.O>CN(C)C=O>[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 23432392HCID 23432392, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

40 g of 4-(4-hydroxyphenyl)benzonitrile, 42 g of potassium carbonate, and 250 g of 1,6-dibromohexane were mixed. The resultant mixture was then caused to react in dimethylformamide at 100° C. for 5 hours. After cooled, the resultant was poured into 1 L of water and extracted with chloroform. The resultant was purified by silica gel column chromatography, and then recrystallized from chloroform/hexane, to give the target compound (yielded amount 39 g, and yield 54%).

Workup

  1. temperatureAfter cooled
  2. extractionextracted with chloroform
  3. customThe resultant was purified by silica gel column chromatography
  4. customrecrystallized from chloroform/hexane
  5. customto give
  6. customthe target compound (yielded amount 39 g, and yield 54%)

Sources & evidence

ORD record
ord-ac1d91678e2b4a6b853a7422cc4e6e9f
Source dataset
uspto-grants-2011_07
Patent number
US07977491B2

Reaction notes

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