Reaction #955906

ord-59f97099726740b49f95823af1fe8a5d

Reaction equation

NN.O
hydrazine monohydrate
C=CC(=O)OC(CCCCCCCCCCCCCCCCC)Oc1cc([N+](=O)[O-])cc(OCCCCCCCCCCCCCCCCCC)c1OCCCCCCCCCCCCCCCCCC
3-(1′-acryloyloxyoctadecyloxy)-4,5-dioctadecyloxy nitrobenzene
→
C=CC(=O)OC(CCCCCCCCCCCCCCCCC)Oc1cc(N)cc(OCCCCCCCCCCCCCCCCCC)c1OCCCCCCCCCCCCCCCCCC
3-(1′-acryloyloxyoctadecyloxy)-4,5-dioctadecyloxy aniline
Yield 71.4%

Reactants

NN.O
hydrazine monohydrate
—
graphite
C=CC(=O)OC(CCCCCCCCCCCCCCCCC)Oc1cc([N+](=O)[O-])cc(OCCCCCCCCCCCCCCCCCC)c1OCCCCCCCCCCCCCCCCCC
3-(1′-acryloyloxyoctadecyloxy)-4,5-dioctadecyloxy nitrobenzene

Reagents

None

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturevia heat-refluxing for 24 hours
  2. 2
    OtherVia recrystallized
  3. 3
    workup.ADDITIONfrom mix solution of chloroform-methanol

Procedure

Thereafter, loaded were 3 ml of hydrazine monohydrate and 10 ml of ethanol in the presence of graphite, 3.9 g of 3-(1′-acryloyloxyoctadecyloxy)-4,5-dioctadecyloxy nitrobenzene was reduced via heat-refluxing for 24 hours. Via recrystallized from mix solution of chloroform-methanol to obtain 2.7 g of 3-(1′-acryloyloxyoctadecyloxy)-4,5-dioctadecyloxy aniline (yield: 71%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08968591B2uspto-grants-2015_03