Potassium Carbonate → 4'-(6-Hydroxyhexyloxy)-4-cyanobiphenyl

HRID 742517Notes

Reaction equation

HRID 742517 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29]>CC(=O)CC>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 779706-Bromo-1-hexanolHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 111739504'-(6-Hydroxyhexyloxy)-4-cyanobiphenylYield 66.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 0.10 g (0.51 mmol) of 4-cyano-4'-hydroxybiphenyl and 0.10 g (0.72 mmol) of potassium carbonate dissolved in 4 ml of 2-butanone was refluxed. After addition of 0.10 g (0.55 mmol) of 6-bromohexan-1-ol to the reaction mixture, the whole was refluxed overnight. After removal of the solvent by distillation, water was added to the residue and the whole was extracted with methylene chloride. The extract was purified by silica gel column chromatography. The resulting white solid was recrystallized from hexane to obtain 0.10 g of 4-cyano-4'(6-hydroxyhexyloxy)biphenyl (9) (yield: 66.4%).

Workup

  1. temperaturewas refluxed
  2. temperaturethe whole was refluxed overnight
  3. customAfter removal of the solvent
  4. distillationby distillation, water
  5. additionwas added to the residue
  6. extractionthe whole was extracted with methylene chloride
  7. customThe extract was purified by silica gel column chromatography
  8. customThe resulting white solid was recrystallized from hexane

Sources & evidence

ORD record
ord-a4aec412ed7c4501bd3e94d2221f3d52
Source dataset
uspto-grants-1996_09
Patent number
US05554706

Reaction notes

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