Ethylene Glycol → 4-Pentyl-4'-biphenylcarboxylic Acid

HRID 462131Notes

Reaction equation

HRID 462131 reaction equation
C(C1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#N.[CH2:20]([OH:23])[CH2:21]O.[OH-:24].[Na+]>O>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:21]([C:20]([OH:23])=[O:24])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 923194-Cyano-4'-pentylbiphenyl

Product 1

HCID 20633354-Pentyl-4'-biphenylcarboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

5 g. 4-cyano-4'-n-pentylbiphenyl in a mixture of 90 ml. ethylene glycol, 18 ml. water and 3.2 g. sodium hydroxide are heated while stirring to 125° C. for 8 hours. After cooling, the reaction mixture is filtered, the residue suspended in 50 ml. ethanol and acidified with 5% hydrochloric acid to a pH of about 2. The reaction mixture is further stirred for 4 hours at room temperature, then filtered and the residue washed with ethanol. The 4-(4-n-pentylphenyl)-benzoic acid obtained is recrystallized from chloroform; m.p. 174° C., S/N 200° C., K. 254° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. stirringThe reaction mixture is further stirred for 4 hours at room temperature
  4. filtrationfiltered
  5. washthe residue washed with ethanol

Sources & evidence

ORD record
ord-7e190bbadd2c4a9a970d50220bb2dfac
Source dataset
uspto-grants-1977_12
Patent number
US04065489

Reaction notes

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