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

HRID 2184525Notes

Reaction equation

HRID 2184525 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-tetralone

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 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-1as an amber oil.

Workup

  1. temperatureat reflux under nitrogen for 45 minutes
  2. customThe: reaction
  3. additionAfter total addition
  4. temperaturethe reaction was heated
  5. temperatureto reflux
  6. stirringstirred under nitrogen for 21 hours
  7. temperatureThe reaction was cooled to ambient temperature
  8. filtrationfiltered
  9. washThe filter cake was washed well with acetone
  10. concentrationthe filtrate was concentrated
  11. customto yield 2.0 g 6-(3-chloropropoxy)-7-methoxy-1as an amber oil

Sources & evidence

ORD record
ord-d3f0bdf7235e40568e1340a54eaa43f9
Source dataset
uspto-grants-2002_06
Patent number
USRE037729E1

Reaction notes

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