Potassium Carbonate → 6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

HRID 1631198Notes

Reaction equation

HRID 1631198 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(Br)C1C=CC=CC=1>[CH2:5]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2)[C:4]1[CH:9]=[CH:10][CH:11]=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 106822416-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-oneYield 182.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 7498Benzyl BromideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 6-hydroxy-3,4-dihydronaphthalen-1(2H)-one (24.3 g) in acetone (160 mL), benzyl bromide (29.4 mL) and potassium carbonate (31.1 g) were added at room temperature, followed by stirring at 40° C. for 3.5 hours. After filtering off the insoluble matters and concentrating the mixture, the residue was washed with a mixed solvent of tert-butyl methyl ether-hexane (1:4) to thereby give the title compound (34.5 g) having the following physical properties.

Workup

  1. filtrationAfter filtering off the insoluble matters
  2. concentrationconcentrating the mixture
  3. washthe residue was washed with a mixed solvent of tert-butyl methyl ether-hexane (1:4)

Sources & evidence

ORD record
ord-9f368a391ad9499d98775b1f4ca850fe
Source dataset
uspto-grants-2014_07
Patent number
US08791159B2

Reaction notes

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