Hydrochloric Acid → 4'-Hexyl[1,1'-biphenyl]-4-carboxylic acid

HRID 328305Notes

Reaction equation

HRID 328305 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17]C(C#N)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(O)CO[CH2:24][CH2:25][OH:26].[OH-:28].[Na+].Cl>O>[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:24]([C:25]([OH:26])=[O:28])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 387644-Hexyl-4'-cyanobiphenyl

Product 1

HCID 135545884'-Hexyl[1,1'-biphenyl]-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 Gram of 4-n-hexyl-4'-cyanobiphenyl, 40 ml of diethylene glycol, 4 ml of water and 2 g of sodium hydroxide were introduced into 200 ml three neck flask and heated with stirring for 25 hours, followed by acidifying with hydrochloric acid, separating by filtration and recrystallizing with glacial acetic acid to give 4.1 g of 4-n-hexyl-biphenyl-4'-carboxylic acid (II), which was a colorless crystal having a molecular formula of C19H22O2 (composition: C 80.8%, H 7.9%, O 11.3% as calculated values and C 80.4%, H 8.1%, O 11.5% as observed values) and a melting point of 170° -171° C and formed a smectic liquid crystal at temperatures exceeding the melting point.

Workup

  1. temperatureheated
  2. customseparating by filtration
  3. customrecrystallizing with glacial acetic acid

Sources & evidence

ORD record
ord-baf99e0fdc284093a7109547019dea7d
Source dataset
uspto-grants-1977_04
Patent number
US04017416

Reaction notes

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