Butyl bromide → 6-Butoxy-3,4-dihydronaphthalen-1(2H)-one

HRID 1656811Notes

Reaction equation

HRID 1656811 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+].Br[CH2:20][CH2:21][CH2:22][CH3:23]>CC(C)=O>[CH2:20]([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)[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 130673356-Butoxy-3,4-dihydronaphthalen-1(2H)-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2.50 g of 6-hydroxy-1-tetralone in 20 ml of acetone, 2.54 g of potassium carbonate and 2 ml of 1-bromobutane were heated under reflux for four days. After evaporation the residue was diluted carefully in 20 ml of 1N hydrochloric acid and extracted three times with ethyl acetate. Then the extracts were washed with aqueous saturated solutions of sodium hydrogen carbonate and sodium chloride and dried over sodium sulfate. After evaporation the resulting residue was purified by chromatography with diethyl ether/petroleum ether (1:2) to yield 3.08 g (91.5% of the theoretical yield) of 6-n-butoxy-1-tetralone in the form of a nearly colorless oil.

Workup

  1. temperatureunder reflux for four days
  2. customAfter evaporation the residue
  3. additionwas diluted carefully in 20 ml of 1N hydrochloric acid
  4. extractionextracted three times with ethyl acetate
  5. washThen the extracts were washed with aqueous saturated solutions of sodium hydrogen carbonate and sodium chloride
  6. dry with materialdried over sodium sulfate
  7. customAfter evaporation the resulting residue
  8. customwas purified by chromatography with diethyl ether/petroleum ether (1:2)
  9. customto yield 3.08 g (91.5% of the

Sources & evidence

ORD record
ord-69da932f1a0b40f091c39f7bd8a762b1
Source dataset
uspto-grants-1993_10
Patent number
US05254731

Reaction notes

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