Potassium Hydroxide → HCID 18971052, compound

HRID 2395201Notes

Reaction equation

HRID 2395201 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]([F:29])([F:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-:30].[K+]>O1CCCC1>[OH:30][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][CH2:8][CH2:9][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][C:17]([F:28])([F:29])[C:18]([F:26])([F:27])[C:19]([F:24])([F:25])[C:20]([F:21])([F:22])[F:23])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22465771HCID 22465771, compound

Product 1

HCID 18971052HCID 18971052, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flask, 1.7 g of 4-hydroxy-4'-[2-(perfluorobutyl)ethyloxy]biphenyl and 10 ml of tetrahydrofuran were placed. To this solution, 3.9 ml of a 1N aqueous solution of potassium hydroxide was added and stirred for a while. After the solvent was distilled away under a reduced pressure, 15 ml of methanol and 0.85 g of 8-bromooctanol were added to the solution and stirred under reflux for 12 hours. Next, the reaction solution was poured into water, and an organic layer was extracted with ether. The ether layer was washed with dilute hydrochloric acid and water in this order. After the solvent was distilled away, the residue was purified by silica gel column chromatography (eluent: benzene/ethyl acetate=9/1), and recrystallized from toluene to give 1.5 g of 4-(8-hydroxyoctyloxy)-4'-[2-(perfluorobutyl)ethyloxy]biphenyl (Y: 67.2%). The purity of the compound thus obtained was 98.8% by GC.

Workup

  1. distillationAfter the solvent was distilled away under a reduced pressure, 15 ml of methanol and 0.85 g of 8-bromooctanol
  2. additionwere added to the solution
  3. stirringstirred
  4. temperatureunder reflux for 12 hours
  5. additionNext, the reaction solution was poured into water
  6. extractionan organic layer was extracted with ether
  7. washThe ether layer was washed with dilute hydrochloric acid and water in this order
  8. distillationAfter the solvent was distilled away
  9. customthe residue was purified by silica gel column chromatography (eluent: benzene/ethyl acetate=9/1)
  10. customrecrystallized from toluene

Sources & evidence

ORD record
ord-d8e979e009d34053b5fc80f864c38a12
Source dataset
uspto-grants-1998_09
Patent number
US05814378

Reaction notes

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