Reaction #955905

ord-20dc7bb1f6b8447e804302ceccdeaa40

Reaction equation

CCCCCCCCCCCCCCCCCCOc1cc([N+](=O)[O-])cc(OC(O)CCCCCCCCCCCCCCCCC)c1OCCCCCCCCCCCCCCCCCC
3-(1′-hydroxyoctadecyloxy)-4,5-dioctadecyloxy nitrobenzene
C=CC(=O)Cl
acryl chloride
→
C=CC(=O)OC(CCCCCCCCCCCCCCCCC)Oc1cc([N+](=O)[O-])cc(OCCCCCCCCCCCCCCCCCC)c1OCCCCCCCCCCCCCCCCCC
3-(1′-acryloyloxyoctadecyloxy)-4,5-dioctadecyloxy nitrobenzene
Yield 92.2%

Reactants

CCCCCCCCCCCCCCCCCCOc1cc([N+](=O)[O-])cc(OC(O)CCCCCCCCCCCCCCCCC)c1OCCCCCCCCCCCCCCCCCC
3-(1′-hydroxyoctadecyloxy)-4,5-dioctadecyloxy nitrobenzene
C=CC(=O)Cl
acryl chloride

Reagents

None

Solvents

c1ccncc1
pyridine

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Othercontrolled at 0° C.
  2. 2
    workup.DISSOLUTIONdissolved
  3. 3
    Otherthe reaction
  4. 4
    Otherresulting solution
  5. 5
    Otherwas purified via silica gel chromatography (mix solvent of hexane and ethyl acetate)

Procedure

Subsequently, into pyridine controlled at 0° C., dissolved was 4.0 g of 3-(1′-hydroxyoctadecyloxy)-4,5-dioctadecyloxy nitrobenzene and added 0.50 g of acryl chloride for 30 minutes, followed by stirring 1 hour at room temperature. After finishing the reaction, resulting solution was purified via silica gel chromatography (mix solvent of hexane and ethyl acetate) to obtain 3.9 g of 3-(1′-acryloyloxyoctadecyloxy)-4,5-dioctadecyloxy nitrobenzene (yield: 92%).

Source

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