4-but-3-enylbenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.4 g of a monohydrate of hydrazine and 45 g of 4-(3-butenyl)benzaldehyde were dissolved in 80 ml of methanol. The mixture was stirred at room temperature for 2 hours. To the mixture was then added 150 ml of dichloromethane. The mixture was then washed with saturated aqueous solution of sodium bicarbonate twice. The mixture was then dehydrated and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting crude reaction product was purified through basic alumina column chromatography, and then recrystallized from methanol to obtain 42 g of 1,2-bis[4-(3-butenyl)benzylidene]hydrazine. The compound thus obtained had a melting point of 57° C. and exhibited nematic phase up to 116° C. The mixture was then washed with saturated aqueous solution of sodium bicarbonate twice dried over anhydrous sodium sulfate The solvent was then distilled off under reduced pressure The resulting crude reaction product was purified through basic alumina column chromatography recrystallized from methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.4 g of a monohydrate of hydrazine and 45 g of 4-(3-butenyl)benzaldehyde were dissolved in 80 ml of methanol. The mixture was stirred at room temperature for 2 hours. To the mixture was then added 150 ml of dichloromethane. The mixture was then washed with saturated aqueous solution of sodium bicarbonate twice. The mixture was then dehydrated and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting crude reaction product was purified through basic alumina column chromatography, and then recrystallized from methanol to obtain 42 g of 1,2-bis[4-(3-butenyl)benzylidene]hydrazine. The compound thus obtained had a melting point of 57° C. and exhibited nematic phase up to 116° C. The mixture was then washed with saturated aqueous solution of sodium bicarbonate twice dried over anhydrous sodium sulfate The solvent was then distilled off under reduced pressure The resulting crude reaction product was purified through basic alumina column chromatography recrystallized from methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 15.6 g of a monohydrate of hydrazine was added a solution of 5.0 g of 4-(3-butenyl)benzaldehyde (synthesized by reacting 1-(3-butenyl)-4-bromobenzene with magnesium to prepare a Grignard reagent which is then reacted with DMF) in 20 ml of ethanol. The mixture was stirred at room temperature for 30 minutes. To the mixture was then added 20 ml of saturated aqueous solution of sodium bicarbonate. To the mixture was then added 10 ml of dichloromethane. The mixture was then washed with 10 ml of saturated aqueous solution of sodium bicarbonate twice. To the resulting organic phase was then added 3.5 ml of triethylamine. The mixture was then dehydrated and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. To the residue was then added 3.5 ml of triethylamine. To the mixture were then added 20 ml of ethanol and 3.75 g of 4-methylbenzaldehyde. The mixture was then stirred at room temperature for 3 hours. To the mixture was then added 20 ml of saturated aqueous solution of sodium bicarbonate. To the mixture was then added 10 ml of dichloromethane. The mixture was then washed with 10 ml of saturated aqueous solution of sodium bicarbonate. The solvent was then distilled off under reduced pressure. The residue was purified through alumina (basic) column chromatography (dichloromethane), and then recrystallized from methanol to obtain 7.0 g of 1-[4-(3-butenyl)benzylidene]-2-(4-methylbenzylidene)hydrazine. The compound thus obtained had a melting point of 82° C. and exhibited nematic phase up to 103° C. synthesized The mixture was then washed with 10 ml of saturated aqueous solution of sodium bicarbonate twice To the resulting organic phase was then added 3.5 ml of triethylamine dried over anhydrous sodium sulfate The solvent was then distilled off under reduced pressure To the residue was then added 3.5 ml of triethylamine To the mixture were then added 20 ml of ethanol and 3.75 g of 4-methylbenzaldehyde The mixture was then stirred at room temperature for 3 hours To the mixture was then added 20 ml of saturated aqueous solution of sodium bicarbonate To the mixture was then added 10 ml of dichloromethane The mixture was then washed with 10 ml of saturated aqueous solution of sodium bicarbonate The solvent was then distilled off under reduced pressure The residue was purified through alumina (basic) column chromatography (dichloromethane) recrystallized from methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.4 g of a monohydrate of hydrazine and 45 g of 4-(3-butenyl)benzaldehyde were dissolved in 80 ml of methanol. The mixture was stirred at room temperature for 2 hours. To the mixture was then added 150 ml of dichloromethane. The mixture was then washed with saturated aqueous solution of sodium bicarbonate twice. The mixture was then dehydrated and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting crude reaction product was purified through basic alumina column chromatography, and then recrystallized from methanol to obtain 42 g of 1,2-bis[4-(3-butenyl)benzylidene]hydrazine. The compound thus obtained had a melting point of 57° C. and exhibited nematic phase up to 116° C. The mixture was then washed with saturated aqueous solution of sodium bicarbonate twice dried over anhydrous sodium sulfate The solvent was then distilled off under reduced pressure The resulting crude reaction product was purified through basic alumina column chromatography recrystallized from methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 15.6 g of a monohydrate of hydrazine was added a solution of 5.0 g of 4-(3-butenyl)benzaldehyde (synthesized by reacting 1-(3-butenyl)-4-bromobenzene with magnesium to prepare a Grignard reagent which is then reacted with DMF) in 20 ml of ethanol. The mixture was stirred at room temperature for 30 minutes. To the mixture was then added 20 ml of saturated aqueous solution of sodium bicarbonate. To the mixture was then added 10 ml of dichloromethane. The mixture was then washed with 10 ml of saturated aqueous solution of sodium bicarbonate twice. To the resulting organic phase was then added 3.5 ml of triethylamine. The mixture was then dehydrated and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. To the residue was then added 3.5 ml of triethylamine. To the mixture were then added 20 ml of ethanol and 3.75 g of 4-methylbenzaldehyde. The mixture was then stirred at room temperature for 3 hours. To the mixture was then added 20 ml of saturated aqueous solution of sodium bicarbonate. To the mixture was then added 10 ml of dichloromethane. The mixture was then washed with 10 ml of saturated aqueous solution of sodium bicarbonate. The solvent was then distilled off under reduced pressure. The residue was purified through alumina (basic) column chromatography (dichloromethane), and then recrystallized from methanol to obtain 7.0 g of 1-[4-(3-butenyl)benzylidene]-2-(4-methylbenzylidene)hydrazine. The compound thus obtained had a melting point of 82° C. and exhibited nematic phase up to 103° C. synthesized The mixture was then washed with 10 ml of saturated aqueous solution of sodium bicarbonate twice To the resulting organic phase was then added 3.5 ml of triethylamine dried over anhydrous sodium sulfate The solvent was then distilled off under reduced pressure To the residue was then added 3.5 ml of triethylamine To the mixture were then added 20 ml of ethanol and 3.75 g of 4-methylbenzaldehyde The mixture was then stirred at room temperature for 3 hours To the mixture was then added 20 ml of saturated aqueous solution of sodium bicarbonate To the mixture was then added 10 ml of dichloromethane The mixture was then washed with 10 ml of saturated aqueous solution of sodium bicarbonate The solvent was then distilled off under reduced pressure The residue was purified through alumina (basic) column chromatography (dichloromethane) recrystallized from methanol