Hydrochloric Acid → HCID 20399051, compound

HRID 1981280Notes

Reaction equation

HRID 1981280 reaction equation
[CH2:1]([C:6]12[CH2:13][CH2:12][C:9]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH3:5].S(Cl)(Cl)=O.[C:27]([C:29]1[C:34]([C:35]#[N:36])=[C:33]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH:32]=[CH:31][C:30]=1O)#[N:28].Cl>N1C=CC=CC=1>[CH2:1]([C:6]12[CH2:7][CH2:8][C:9]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([O:20][C:30]4[CH:31]=[CH:32][C:33]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[C:34]([C:35]#[N:36])[C:29]=4[C:27]#[N:28])=[O:19])=[CH:16][CH:15]=3)([CH2:10][CH2:11]1)[CH2:12][CH2:13]2)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 129479444-(4-Pentylbicyclo[2.2.2]octan-1-yl)benzoic acidHCID 203990393-Hydroxy-6-pentylbenzene-1,2-dicarbonitrile

Product 1

HCID 20399051HCID 20399051, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

36.5 mmoles of 4-(4-pentyl-1-bicyclo(2,2,2)-octyl)-benzoic acid were refluxed with 50 ml of thionyl chloride for 1 hour. The excess thionyl chloride was distilled off. The resulting acid chloride was added dropwise to a solution of 36.5 mmoles of 2,3-dicyano-4-pentylphenol in 100 ml of pyridine. The reaction mixture was stirred at 80° C. until the reaction had ended and was then poured onto dilute hydrochloric acid. The product was extracted with methylene chloride. For purification, the product was recrystallized. It displays an enantiotropic nematic phase (K 130.9 N (137.9) I) and has a negative DCA.

Workup

  1. distillationThe excess thionyl chloride was distilled off
  2. extractionThe product was extracted with methylene chloride
  3. customFor purification
  4. customthe product was recrystallized

Sources & evidence

ORD record
ord-adf91562ba9149e5bf929ccc7504786b
Source dataset
uspto-grants-1985_04
Patent number
US04514317

Reaction notes

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