1,3-Dinitrobenzene → 1-Phenoxy-3-vinylbenzene

HRID 1065534Notes

Reaction equation

HRID 1065534 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14](O)[CH3:15])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=CC=C([N+]([O-])=O)C=1)([O-])=O>CS(C)=O>[O:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[CH:14]=[CH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 74521,3-DinitrobenzeneHCID 128824191-(3-Phenoxyphenyl)ethanol

Product 1

HCID 98370411-Phenoxy-3-vinylbenzeneYield 74.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 250 ml. of dimethyl sulfoxide were dissolved 7.0 g of α-(3-phenoxyphenyl)ethyl alcohol and 0.5 g of m-dinitrobenzene as a polymerization inhibitor. The solution was subjected to reaction at 160° C. for 10 hours. After cooling, the reaction mixture was incorporated with 250 ml. of dichloromethane, and washed with 600 ml. of water. The resultant dichloromethane layer was separated after removal of the dimethyl sulfoxide, and dried with magnesium sulfate. Then the dichloromethane in the layer was distilled off under reduced pressure, and the resultant residue was subjected to column chromatography. From hexane eluate was obtained 4.75 g of 3-phenoxystyrene.

Workup

  1. customThe solution was subjected to reaction at 160° C. for 10 hours
  2. temperatureAfter cooling
  3. washof dichloromethane, and washed with 600 ml
  4. customThe resultant dichloromethane layer was separated
  5. customafter removal of the dimethyl sulfoxide
  6. dry with materialdried with magnesium sulfate
  7. distillationThen the dichloromethane in the layer was distilled off under reduced pressure

Sources & evidence

ORD record
ord-74131b7c8a204284933f69cb114677f8
Source dataset
uspto-grants-1982_05
Patent number
US04329507

Reaction notes

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