Allyl bromide → 1-Allyloxy-3-phenyl-7-nitronaphthalene

HRID 364667Notes

Reaction equation

HRID 364667 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([OH:20])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[CH:28]=[CH2:29]>CC(C)=O>[CH2:29]([O:20][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)[CH:16]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=1)[CH:28]=[CH2:27]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 1216157-Nitro-3-phenyl-1-naphthol

Product 1

HCID 202396591-Allyloxy-3-phenyl-7-nitronaphthalene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 125 g of 3-phenyl-7-nitro-1-naphthol prepared in step (2), 65 g of anhydrous potassium carbonate, 95 g of allyl bromide and 1200 ml of acetone was refluxed for 4 hours with good stirring. After cooling, the mineral salts were removed by filtration and the residual organic solution was evaporated to dryness under reduced pressure. The crystals thus formed were washed with petroleum ether, filtered and dried at 80° C. under reduced pressure.

Workup

  1. temperaturewas refluxed for 4 hours with good stirring
  2. temperatureAfter cooling
  3. customthe mineral salts were removed by filtration
  4. customthe residual organic solution was evaporated to dryness under reduced pressure
  5. customThe crystals thus formed
  6. washwere washed with petroleum ether
  7. filtrationfiltered
  8. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-3bd0a752f94a4d40a8fc8ab1fb0d33ad
Source dataset
uspto-grants-1986_08
Patent number
US04605697

Reaction notes

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