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

HRID 1899504Notes

Reaction equation

HRID 1899504 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-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. 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-e14b3bd7719c4f46beaa47915e32f4e3
Source dataset
uspto-grants-1996_11
Patent number
US05571828

Reaction notes

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