Benzyl Bromide → 5-(Benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1271264Notes

Reaction equation

HRID 1271264 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:13]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1199215-Hydroxy-1-tetralone

Product 1

HCID 105869155-(Benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-oneYield 87.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4.86 g of 5-hydroxy-1-tetralone in 50 ml of acetonitrile, 5.13 g of benzyl bromide and 6.22 g of potassium carbonate were added and the mixture was heated at reflux for 4 hours. The insoluble matter was removed by filtration and the filtrate was concentrated. The residue was purified by silica gel column chromatography to obtain 6.62 g of the desired compound as a pale yellow oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customThe insoluble matter was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b8d41c52c76e4f0aa2b999fa80ced6aa
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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