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

HRID 2269954Notes

Reaction equation

HRID 2269954 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-3f2aac6855df403bb6f8b06c8df0373f
Source dataset
uspto-grants-2001_12
Patent number
USRE037478E1

Reaction notes

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