Dichloromethane → 1,2-Bis[4-(3-butenyl)benzylidene]hydrazine

HRID 848942Notes

Reaction equation

HRID 848942 reaction equation
[NH2:1][NH2:2].[CH2:3]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)[CH2:4][CH:5]=[CH2:6].ClCCl>CO>[CH2:3]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[N:1][N:2]=[CH:11][C:10]2[CH:13]=[CH:14][C:7]([CH2:3][CH2:4][CH:5]=[CH2:6])=[CH:8][CH:9]=2)=[CH:9][CH:8]=1)[CH2:4][CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 193682444-(But-3-en-1-yl)benzaldehyde

Product 1

HCID 539291401,2-Bis[4-(3-butenyl)benzylidene]hydrazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. washThe mixture was then washed with saturated aqueous solution of sodium bicarbonate twice
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was then distilled off under reduced pressure
  4. customThe resulting crude reaction product
  5. customwas purified through basic alumina column chromatography
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-6fbaee54e5a146a6a9b2628dc0a82ee1
Source dataset
uspto-grants-2000_01
Patent number
US06010642

Reaction notes

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