Hydrochloric Acid → HCID 178448006, compound

HRID 1165112Notes

Reaction equation

HRID 1165112 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]3[CH:21]=[C:22]([F:26])[CH:23]=[CH:24][CH:25]=3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)[CH2:6][CH3:7].[C:27](Cl)(=[O:29])[CH3:28].Cl>[N+](C1C=CC=CC=1)([O-])=O.C1(C)C=CC=CC=1>[C:27]([C:23]1[CH:24]=[CH:25][C:20]([C@H:17]2[CH2:18][CH2:19][C@H:14]([C@H:11]3[CH2:10][CH2:9][C@H:8]([CH2:5][CH2:6][CH3:7])[CH2:13][CH2:12]3)[CH2:15][CH2:16]2)=[CH:21][C:22]=1[F:26])(=[O:29])[CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178448007HCID 178448007, compound

Product 1

HCID 178448006HCID 178448006, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7416NitrobenzeneSolvent

Procedure

Successively, anhydrous aluminum chloride (30.8 g, 0.23 mol) was dissolved in nitrobenzene (150 ml), followed by adding to the solution, the total quantity of the above compound 3-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]fluorobenzene (38.7 g) at room temperature, dissolving the mixture together with stirring, adding acetyl chloride (27.3 g, 0.348 mol) over 15 minutes, reacting the mixture on heating at a reaction temperature of 35°-40° C. for 2 hours, adding the reaction solution after completion of the reaction to a mixture of 6N hydrochloric acid (50 ml) with ice water (500 g) to subject them to decomposition reaction, adding toluene (500 ml) to extract the resulting oily layer, washing the extract solution with an aqueous solution of sodium hydrogen carbonate, further washing it with water until the washing water became neutral, distilling off toluene and nitrobenzene and recrystallizing the residue from ethyl acetate to obtain 2-acetyl-5-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]fluorobenzene (a compound of the formula (VII) wherein R1 =C3H7 and R"=CH3) (23.8 g). This product exhibited liquid crystal phases and had a crystal-nematic phase transition point (C-N point) of 90.5° C. and a nematic phase-isotropic liquid phase transition point (N-I point) of 204.7° C. (iii) Successively, the compound 2-acetyl-5-[trans-4-(trans-4-propylcyclohexyl) cyclohexyl]fluorobenzene (23.8 g) was added to diethylene glycol (100 ml), followed by agitating the mixture, adding hydrazine hydrate (17.9 g) and potassium hydroxide (20.1 g), gradually raising the temperature with stirring to react the mixture at 180° C. for 3 hours, allowing the resulting material to cool down to room temperature, adding water (500 ml), extracting the deposited crystals with toluene (100 ml), washing the extract solution with water, drying it over anhydrous sodium sulfate, distilling off toluene and recrystallizing from ethyl acetate to obtain 2-ethyl-5-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]fluorobenzene (15.2 g).

Workup

  1. additionby adding to the solution
  2. temperatureon heating at a reaction temperature of 35°-40° C. for 2 hours
  3. additionadding the reaction solution
  4. customafter completion of the reaction
  5. customto decomposition reaction
  6. extractionto extract the resulting oily layer
  7. washwashing the extract solution with an aqueous solution of sodium hydrogen carbonate
  8. washfurther washing it with water until the washing water
  9. distillationdistilling off toluene and nitrobenzene
  10. customrecrystallizing the residue from ethyl acetate

Sources & evidence

ORD record
ord-2d0aefba07554898a4272949dd16bd2a
Source dataset
uspto-grants-1990_03
Patent number
US04908152

Reaction notes

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