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

HRID 1088426Notes

Reaction equation

HRID 1088426 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-b927fdef7a274726823eba9f571544a1
Source dataset
uspto-grants-1990_10
Patent number
US04962160

Reaction notes

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