Acrylonitrile → HCID 22161304, compound

HRID 1088595Notes

Reaction equation

HRID 1088595 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([N:13]=[N:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].C[N+:24](C)(C)[CH2:25][C:26]1C=CC=C[CH:27]=1.C(#N)C=C>C1C=CC=CC=1>[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([N:13]=[N:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:26]([CH3:27])[C:25]#[N:24])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 13570282833228-49-8

Product 1

HCID 22161304HCID 22161304, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 2 ml of benzene, 0.4 g of 4-hexyl-4'-hydroxyazobenzene and a catalytic amount of trimethylbenzylammonium hydroxide were dissolved. To the resultant solution, 8 ml of acrylonitrile was slowly added. The resultant mixture was heated for 22 hours and then subjected to vacuum distillation for expulsion of the solvent. The residue of the distillation was extracted with benzene. Then, it was purified by silica gel column chromatography, to obtain 0.25 g of 2-[4-(4-hexylphenylazo)phenoxy]propanenitrile. This compound was converted to a corresponding carboxylic acid by hydrolysis with acetic acid containing hydrochloric acid. The carboxylic acid was converted into an acid chloride with thionyl chloride. The aminated quartz plates were treated with the acid chloride in the same manner as in Example 18. The absorption spectrum of the quartz plates indicated that the plates had azobenzene bonded thereto. A sandwich cell was produced by interposing the same mixed such a manner that the direction of rubbing perpendicularly intersected. When this cell was exposed alternately to an ultraviolet light and a visible light, it showed a reversible change in transmittance, indicating a change in the arrangement of liquid crystals between the homeotropic mode and the twisted mode.

Workup

  1. distillationsubjected to vacuum distillation for expulsion of the solvent
  2. distillationThe residue of the distillation
  3. extractionwas extracted with benzene
  4. customThen, it was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-af70523fc74c42ea872c0069fda01bf0
Source dataset
uspto-grants-1990_10
Patent number
US04963448

Reaction notes

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