1-Bromo-3-chloropropane → HCID 67070939, compound

HRID 1955869Notes

Reaction equation

HRID 1955869 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6](O)=[C:5]([O:10][CH3:11])[CH:4]=1)[CH3:2].[Cl:12][CH2:13][CH2:14][CH2:15]Br.C([O-])([O-])=[O:18].[K+].[K+]>CC(C)=O>[CH2:1]([C:3]1([O:18][CH2:15][CH2:14][CH2:13][Cl:12])[CH:8]=[CH:7][CH:6]=[C:5]([O:10][CH3:11])[CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 624654-Ethylguaiacol

Product 1

HCID 67070939HCID 67070939, compoundYield 115%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-ethyl-2-methoxyphenol (9.0 g, 59 mmol), 3-chloro-1-bromopropane (13.0 g, 83 mmol), K2CO3 (6.2 g) and acetone (200 ml) was stirred and refluxed for 16 hours. The reaction was allowed to cool, and then it was filtered. The filtrate was concentrated to a clear liquid. The liquid was diluted with dilute aqueous NaOH, and the basic mixture was extracted with diethyl ether. The diethyl ether was washed (water), dried (MgSO4), and the solvent was concentrated to afford 11.9 g of a golden liquid. The liquid was flash chromatographed. This gave a colorless liquid, 9.9 g of 4-ethyl-2-methoxy+(3-chloropropoxy)benzene.

Workup

  1. temperaturerefluxed for 16 hours
  2. temperatureto cool
  3. filtrationit was filtered
  4. concentrationThe filtrate was concentrated to a clear liquid
  5. additionThe liquid was diluted with dilute aqueous NaOH
  6. extractionthe basic mixture was extracted with diethyl ether
  7. washThe diethyl ether was washed (water)
  8. dry with materialdried (MgSO4)
  9. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-d3abaaf7bc544b9290765c661ce83bc7
Source dataset
uspto-grants-1998_07
Patent number
US05776963

Reaction notes

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