Water → 4-Pentyl-4'-biphenylcarboxylic Acid

HRID 328304Notes

Reaction equation

HRID 328304 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#N)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].S(=O)(=O)(O)[OH:21].[OH2:25]>>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:21])=[O:25])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 923194-Cyano-4'-pentylbiphenyl

Product 1

HCID 20633354-Pentyl-4'-biphenylcarboxylic Acid

Procedure

50 Gram of 4-n-pentyl-4'-cyanobiphenyl and 500 g of 70 weight % sulfuric acid were introduced into 2 l three neck flask, and heated on a mantle heater, with stirring under reflux for 2.5 hours. The resulting reaction mixture was water-cooled and then 500 ml of water was added, followed by separating a solid product with a glass filter, water-washing and recrystallizing with glacial acetic acid to give 45.7 g of 4-n-pentyl-biphenyl-4'-carboxylic acid((II), R=C5H11) which was a colorless crystal having a molecular formula of C18H20O2 (composition: C 80.6%, H 7.5%, O 11.9% as calculated values and C 80.3%, H 7.6%, O 12.1% as observed values) and a melting point of 177° C, and formed a smectic liquid crystal at temperatures exceeding the melting point.

Workup

  1. temperatureheated on a mantle heater
  2. temperatureunder reflux for 2.5 hours
  3. customThe resulting reaction mixture
  4. temperaturecooled
  5. customby separating a solid product with a glass
  6. filtrationfilter
  7. washwater-washing
  8. customrecrystallizing with glacial acetic acid

Sources & evidence

ORD record
ord-515348f9bf464acfbc2da0158976bc03
Source dataset
uspto-grants-1977_04
Patent number
US04017416

Reaction notes

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