1-Bromo-3-chloropropane → 6-(3-Chloropropoxy)-7-methoxy-1-tetralone

HRID 1781690Notes

Reaction equation

HRID 1781690 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH2:7][CH2:6][CH2:5]2.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][CH2:24][Cl:25]>CC(C)=O>[Cl:25][CH2:24][CH2:23][CH2:22][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 3168396-Hydroxy-7-methoxy-1-tetralone

Product 1

HCID 104457686-(3-Chloropropoxy)-7-methoxy-1-tetraloneYield 95.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 6-hydroxy-7-methoxy-1-tetralone (J. Org. Chem., 1985, 50, 4937) (1.5 g, 7.8 mmol), K2CO3 (1.7 g, 12.3 mmol), and acetone (30 ml) was stirred at reflux under nitrogen for 45 minutes. The reaction was cooled to ambient temperature and a solution of 1-bromo-3-chloropropane (1.9 g, 12.1 mmol) dissolved in 8 ml acetone was dripped into the mixture. After total addition, the reaction was heated to reflux and stirred under nitrogen for 21 hours. The reaction was cooled to ambient temperature and filtered. The filter cake was washed well with acetone and the filtrate was concentrated to yield 2.0 g 6-(3-chloropropoxy)-7-methoxy-1-tetralone as an amber oil.

Workup

  1. temperatureat reflux under nitrogen for 45 minutes
  2. additionAfter total addition
  3. temperaturethe reaction was heated
  4. temperatureto reflux
  5. stirringstirred under nitrogen for 21 hours
  6. temperatureThe reaction was cooled to ambient temperature
  7. filtrationfiltered
  8. washThe filter cake was washed well with acetone
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e35fbcdcb13241568a28c7d7e5bccbf5
Source dataset
uspto-grants-1997_05
Patent number
US05633265

Reaction notes

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