4,4'-Dihydroxybiphenyl → 4,4'-Bis(octyloxy)-1,1'-biphenyl

HRID 1014751Notes

Reaction equation

HRID 1014751 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(O)C>[CH2:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][CH2:8][CH3:9])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 81401-BromooctaneHCID 14797Potassium Hydroxide

Product 1

HCID 438334284,4'-Bis(octyloxy)-1,1'-biphenylYield 170%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

56 g of 4,4′-dihydroxybiphenyl was dissolved in 500 g ethanol. To this solution was added 40 g of potassium hydroxide, and the mixture was reacted. Next, this solution was heated, and 128 g of 1-bromooctane was dropped at 70° C., and subsequently, the mixture was reacted at 70° C. for 7 hours. The reaction was performed under a nitrogen atmosphere. After the reaction, this solution was cooled, and the generated precipitate was filtrated to recover. Next, this precipitate was washed with 500 ml of methanol, then, washed with a mixed solvent of methanol 500 ml/ion exchanged water 300 ml, and further, washed with a mixed solvent of acetone 500 ml/ion exchanged water 300 ml. This precipitate was dried under reduced pressure, to obtain 105 g of 4,4′-dioctyloxybiphenyl represented by the following structural formula:

Workup

  1. customthe mixture was reacted
  2. temperatureNext, this solution was heated
  3. customsubsequently, the mixture was reacted at 70° C. for 7 hours
  4. customAfter the reaction
  5. temperaturethis solution was cooled
  6. filtrationthe generated precipitate was filtrated
  7. customto recover
  8. washNext, this precipitate was washed with 500 ml of methanol
  9. washwashed with a mixed solvent of methanol 500 ml/ion
  10. washfurther, washed with a mixed solvent of acetone 500 ml/ion
  11. customThis precipitate was dried under reduced pressure

Sources & evidence

ORD record
ord-2c1bfbbb8c744e90bad8ab4c340f20b8
Source dataset
uspto-grants-2011_07
Patent number
US07982212B2

Reaction notes

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