Hydrochloric Acid → HCID 178442076, compound

HRID 1632704Notes

Reaction equation

HRID 1632704 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]2=O)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].Cl>O1CCCC1>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:15]3[CH2:16][CH2:17][CH:12]([C@H:9]4[CH2:10][CH2:11][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]4)[CH2:13][CH:14]=3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20442009HCID 20442009, compound

Product 1

HCID 178442076HCID 178442076, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-pentyl-4'-bromobiphenyl (2.8 g, 0.0092 mol) dissolved in tetrahydrofuran (50 ml) was reacted with Mg (0.22 g, 0.0092 mol) in nitrogen current to obtain 4-pentyl-4'-biphenylmagnesium bromide. The reaction liquid was cooled to 0° C. and to this liquid was added a tetrahydrofuran solution (50 ml) of 4-pentylcyclohexylcyclohexanone (2.3 g, 0.0092 mol). The mixture was refluxed at 50° C. for 2 hours and 3N hydrochloric acid (50 ml) was then added, followed by extracting the product with toluene (200 ml), washing with water, distilling off the solvent, adding potassium hydrogen sulfate (4 g) and dehydrating at 200° C. for 2 hours in nitrogen atmosphere. After cooling, toluene (200 ml) was added and potassium hydrogen sulfate was filtered off, followed by washing with water till the washing water became neutral, dehydrating with anhydrous sodium sulfate, distilling off the solvent and recrystallizing from toluene to obtain crystals of 4-pentyl-4'-[4-(trans-4-pentylcyclohexyl)cyclohexen-1-yl]biphenyl. This product (1.4 g, 0.0031 mol) was dissolved in n-heptane (200 ml) and to the solution was added Raney Ni (0.7 g), followed by catalytic reduction under ordinary pressure at 60° C. The reaction was traced by gas chromatography, and when the raw material disappeared, that is, after 12 hours, reduction was completed. Since the resulting material was a mixture of cis-form and trans-form substances, it was recrystallized from toluene to take out the trans-form substance, that is, an objective product, 4-pentyl-4'-[trans-4-(trans-4-pentylcyclohexyl)cyclohexyl]-biphenyl. Yield: 0.5 g (0.001 mol). This product had such a very broad liquid-crystalline temperature range as a C-Sm point of room temperature or lower and a Sm-I point of 300° C. or higher.

Workup

  1. customThe reaction liquid
  2. temperatureThe mixture was refluxed at 50° C. for 2 hours
  3. extractionby extracting the product with toluene (200 ml)
  4. washwashing with water
  5. distillationdistilling off the solvent
  6. additionadding potassium hydrogen sulfate (4 g)
  7. temperatureAfter cooling
  8. additiontoluene (200 ml) was added
  9. filtrationpotassium hydrogen sulfate was filtered off
  10. washby washing with water till the washing water
  11. distillationdistilling off the solvent
  12. customrecrystallizing from toluene

Sources & evidence

ORD record
ord-4b0779c9f2e1455ca5be50d73b8f7f1c
Source dataset
uspto-grants-1984_10
Patent number
US04477369

Reaction notes

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