Toluene → HCID 178435746, compound

HRID 1632706Notes

Reaction equation

HRID 1632706 reaction equation
C(C1C=CC(C2C=CC([C:15]3[CH2:20][CH2:19][CH:18]([C@H:21]4[CH2:26][CH2:25][C@H:24]([CH2:27][CH3:28])[CH2:23][CH2:22]4)[CH2:17][CH:16]=3)=CC=2)=CC=1)C.[C:29]1(Cl)[C:35](=O)[C:34](Cl)=[C:33](Cl)[C:31](=O)[C:30]=1Cl.[C:41]1(C)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[C:48]1(C)C(C)=CC=C[CH:53]=1>>[CH2:27]([C:24]1[CH:23]=[CH:22][C:21]([C:18]2[C:19]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[CH:20][C:15]([C@H:29]3[CH2:35][CH2:34][C@H:33]([CH2:48][CH3:53])[CH2:31][CH2:30]3)=[CH:16][CH:17]=2)=[CH:26][CH:25]=1)[CH3:28]

Participants

5

Reactant 4

HCID 1140TolueneHCID 7237O-XyleneHCID 8371ChloranilHCID 178435675HCID 178435675, compound

Product 1

HCID 178435746HCID 178435746, compound

Procedure

4-Ethyl-4'-[4'-(trans-4-ethylcyclohexyl)cyclohexen-1-yl]biphenyl (11 g, 0.030 mol) was dissolved in xylene (300 ml), and chloranil (16 g, 0.065 mol) was added, followed by reflux for 20 hours. After cooling, toluene (500 ml) was added, followed by washing once with 6N hydrochloric acid and three times with 2N NaOH, washing with saturated NaCl aqueous solution till the washing liquid became neutral, distilling off the solvent under reduced pressure, and recrystallizing from toluene to obtain an objective product, 4-ethyl-4'-(trans-4-ethylcyclohexyl)terphenyl (yield: 5 g) having a C-Sm point of 147.0° C. a Sm-N point of 260° C. and a N-I point of 300° C. or higher.

Workup

  1. temperatureby reflux for 20 hours
  2. temperatureAfter cooling
  3. washby washing once with 6N hydrochloric acid and three times with 2N NaOH
  4. washwashing with saturated NaCl aqueous solution till the washing liquid
  5. distillationdistilling off the solvent under reduced pressure
  6. customrecrystallizing from toluene

Sources & evidence

ORD record
ord-8a7027ee032b4e17855246a878f643b1
Source dataset
uspto-grants-1984_10
Patent number
US04477369

Reaction notes

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