Allyl bromide → 1(2H)-Naphthalenone, 3,4-dihydro-6-(2-propenyloxy)-

HRID 495001Notes

Reaction equation

HRID 495001 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][C:10](O)=[C:9]2O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 136337044HCID 136337044, compound

Product 1

HCID 117012341(2H)-Naphthalenone, 3,4-dihydro-6-(2-propenyloxy)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.30 ml of allyl bromide was added to a mixture consisting of 5.62 g of 6-hydroxy-3,4-dihydroxynaphthalen-1(2H)-one, 5.27 g of potassium carbonate, and 60 ml of acetone. The obtained mixture was heated to reflux under nitrogen atmosphere overnight. The reaction solution was cooled to a room temperature, and the precipitate was removed by filtration. The solvent was removed under a reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 6.35 g of the subject compound.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureto reflux under nitrogen atmosphere overnight
  3. customthe precipitate was removed by filtration
  4. customThe solvent was removed under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ecfd8e5583e44cf2b952aecc7d991ee2
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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