Potassium Hydroxide → 4'-(6-Hydroxyhexyloxy)-4-cyanobiphenyl

HRID 1193463Notes

Reaction equation

HRID 1193463 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25]>CO>[OH:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 779706-Bromo-1-hexanolHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 111739504'-(6-Hydroxyhexyloxy)-4-cyanobiphenylYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 800 ml of a methanol solution having dissolved therein 34 g (0.514 mol) of potassium hydroxide were added 100 g (0.512 mol) of 4-hydroxy-4'-cyanobiphenyl and 93 g (0.512 mol) of 6-bromo-1-hexanol, and the mixture was heated at reflux for 13 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was concentrated under reduced pressure by the use of an evaporator, and the residue was purified by column chromatography using Wakogel C-200 as a carrier and hexane/THF, i.e., tetrahydrofuran as a developing solution to obtain 65 g (yield: 40%) of 4-(6-hydroxyhexyloxy)-4'-cyanobiphenyl.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 13 hours
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract was concentrated under reduced pressure by the use of an evaporator
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9458846dff4d4869bec5e1a095016095
Source dataset
uspto-grants-1989_03
Patent number
US04810433

Reaction notes

Loading…