Ethylene Glycol → 4'-Decyloxybiphenyl-4-carboxylic Acid

HRID 727968

Reaction equation

HRID 727968 reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22]C(C#N)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-:26].[Na+].Cl.[CH2:29]([OH:32])[CH2:30]O>>[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:30]([C:29]([OH:32])=[O:26])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 112405[1,1'-Biphenyl]-4-carbonitrile, 4'-(decyloxy)-

Product 1

HCID 114510854'-Decyloxybiphenyl-4-carboxylic Acid

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. temperatureunder reflux for 4 hours
  2. customThe reaction liquid
  3. temperaturecooled by ice
  4. filtrationthe precipitate was recovered by filtration
  5. washwashed with water and ethanol
  6. customdried
  7. customThe dried product was recrystallized from chloroform

Sources & evidence

ORD record
ord-6bc3b39ad0ab49a4b5ede57a37e082c8
Source dataset
uspto-grants-1991_09
Patent number
US05045228

Linked notes

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