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

HRID 1459951Notes

Reaction equation

HRID 1459951 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-40e85727da944c748ca51ff1a63322af
Source dataset
uspto-grants-1998_12
Patent number
US05854263

Reaction notes

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