1-Bromodecane → [1,1'-Biphenyl]-4-carbonitrile, 4'-(decyloxy)-

HRID 727967

Reaction equation

HRID 727967 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[CH2:17]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 112405[1,1'-Biphenyl]-4-carbonitrile, 4'-(decyloxy)-Yield 97%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To 30 ml of methyl isobutyl ketone were added 3 g of 4-hydroxy-4'-cyanobiphenyl, 21.4 g of 1-bromodecane and 2.5 g of potassium carbonate, and the mixture was reacted under reflux for 30 hours. The reaction mixture was cooled and insoluble substances were removed by filtration. The filtrate was concentrated under a reduced pressure, ethanol was added to the residue and recrystallization was carried out to obtain 5 g of 4-decyloxy-4'-cyanobiphenyl. Thus, 4.1 g of this 4-decyloxy-4'-cyanobiphenyl was dissolved in 25 ml of ethylene glycol, 2.5 ml of 2N sodium hydroxide was added to the solution, and a reaction was carried out under reflux for 4 hours. The reaction liquid was put into dilute hydrochloric acid cooled by ice, and the precipitate was recovered by filtration, washed with water and ethanol, and dried. The dried product was recrystallized from chloroform to obtain 3.0 g of 4'-decyloxybiphenyl-4-carboxylic acid. Then, 20 g of thionyl chloride was dropped into this carboxylic acid and the mixture was reacted under reflux for 2 hours. Unreacted thionyl chloride was removed by distillation under a reduced pressure and 4'-decyloxybiphenyl-4-carboxylic acid chloride was quantitatively recovered.

Workup

  1. customthe mixture was reacted
  2. temperatureunder reflux for 30 hours
  3. temperatureThe reaction mixture was cooled
  4. custominsoluble substances were removed by filtration
  5. concentrationThe filtrate was concentrated under a reduced pressure, ethanol
  6. additionwas added to the residue and recrystallization

Sources & evidence

ORD record
ord-326b98ea0bee497fa1cfc96feb27b4d3
Source dataset
uspto-grants-1991_09
Patent number
US05045228

Linked notes

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