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

HRID 128003Notes

Reaction equation

HRID 128003 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 filration 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 filration
  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-bec2a09f2b0e472dbe04176f4a3cf775
Source dataset
uspto-grants-1981_03
Patent number
US04258120

Reaction notes

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