Benzyl Bromide → 6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

HRID 278455Notes

Reaction equation

HRID 278455 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.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:13]([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:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 106822416-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-oneYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6-Hydroxy-1-tetralone (10 g, 61.65 mmol), benzyl bromide (8.1 ml, 67.82 mmol) and K2CO3 (21.3 g, 154 mmol) in acetone (40 ml) were heated under reflux 2.5 hr. Following filtration and evaporation of the solvent the crude material was acidified to pHl with 1N HCl and partioned between H2O (150 ml) and EtOAc (150 ml). The aqueous phase was further extracted with EtOAc (100 ml) and the extracts dried (Na2SO4) filtered and evaporated to afford 6-benzyloxy-1-tetralone as an orange solid (12.37 g, 49.3 mmol, 80%) Mp. 97-100° C., MS m/e=252.1 (M+).

Workup

  1. temperatureunder reflux 2.5 hr
  2. filtrationfiltration and evaporation of the solvent the crude material
  3. extractionThe aqueous phase was further extracted with EtOAc (100 ml)
  4. dry with materialthe extracts dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c582a9c5b45a437f8e86338b54e7a522
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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