Ethanol → 4-(4-Pentenoxy)-4'-nitrobiphenyl

HRID 2166322Notes

Reaction equation

HRID 2166322 reaction equation
C(O)C.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[OH-].[K+].Br[CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27]>O>[CH2:27]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)[CH2:26][CH2:25][CH:24]=[CH2:23]

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 707041-Pentene, 5-bromo-HCID 1380784-Hydroxy-4'-nitrobiphenyl

Product 1

HCID 199012844-(4-Pentenoxy)-4'-nitrobiphenyl

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 400 ml ethanol is added 21.5 g of 4-hydroxy-4'-nitrobiphenyl, and the mixture heated to reflux. A solution of 7.1 g KOH in 30 ml of water is added dropwise at reflux temperatures. After complete addition, 18 g of 5-bromo-1-pentene is added and the reaction medium is heated at reflux temperature for about 15 hours. Ethanol is removed under vacuum from the cooled mixture, and the solid residue is slurried with water in a blender, filtered, washed with water, and air dried. The product then is recrystallized from 90/10 hexane/toluene, mp 74°-76° C.

Workup

  1. temperaturethe mixture heated to reflux
  2. temperatureat reflux temperatures
  3. additionis added
  4. temperaturethe reaction medium is heated
  5. temperatureat reflux temperature for about 15 hours
  6. customEthanol is removed under vacuum from the cooled mixture
  7. filtrationfiltered
  8. washwashed with water, and air
  9. customdried
  10. customThe product then is recrystallized from 90/10 hexane/toluene, mp 74°-76° C.

Sources & evidence

ORD record
ord-27ea166ff2d249d38a0e5935d0b69506
Source dataset
uspto-grants-1990_07
Patent number
US04944896

Reaction notes

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