Water → 4-(4-Heptylphenyl)benzoic Acid

HRID 328306Notes

Reaction equation

HRID 328306 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#N)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].S(=O)(=O)(O)[OH:23].[OH2:27]>>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:23])=[O:27])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 170468[1,1'-Biphenyl]-4-carbonitrile, 4'-heptyl-

Product 1

HCID 30863554-(4-Heptylphenyl)benzoic Acid

Procedure

50 Gram of 4-n-heptyl-4'-cyanobiphenyl and 500 g of 70 weight % sulfuric acid were introduced into a 2 l three neck flask and heated on a mantle heater with stirring under reflux for 2.5 hours, followed by water-cooling adding 500 ml of water, separating the resulting solid by filtration with a glass filter, water-washing and recrystallizing with glacial acetic acid, to give 47.3 g of 4-n-heptyl-biphenyl-4'-carboxylic acid ((II), R=C7H15), which was a colorless crystal having a molecular formula of C20H24O2 (composition: C 81.0%,H 8.2%, O 10.8% as calculated values and C 81.2%, H 8.3%, O 10.5% as observed values) and a melting point of 163° 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. temperaturecooling
  4. customseparating the resulting solid
  5. filtrationby filtration with a glass
  6. filtrationfilter
  7. washwater-washing
  8. customrecrystallizing with glacial acetic acid

Sources & evidence

ORD record
ord-5cf613c3426c4250888204d44af5aace
Source dataset
uspto-grants-1977_04
Patent number
US04017416

Reaction notes

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