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

HRID 233867Notes

Reaction equation

HRID 233867 reaction equation
O[CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[C:3]1=[O:14].[C:15]([O-:18])([O-])=O.[K+].[K+].BrC[CH2:23][CH2:24][Cl:25]>CC(C)=O>[Cl:25][CH2:24][CH2:23][CH2:15][O:18][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[O:12][CH3:13])[C:3](=[O:14])[CH2:2][CH2:11][CH2:10]2

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 81650156HCID 81650156, compound

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,x 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. additionA mixture of 6
  2. temperatureat reflux under nitrogen for 45 minutes
  3. additionAfter total addition
  4. temperaturethe reaction was heated
  5. temperatureto reflux
  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-9e5ccf53ff8f40daacc6ec55e0774740
Source dataset
uspto-grants-1997_01
Patent number
US05593995

Reaction notes

Loading…