1-Bromo-3-chloropropane → 2-(3-Chloropropoxy)-1,4-dimethoxybenzene

HRID 2256606Notes

Reaction equation

HRID 2256606 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[OH:11].C([O-])([O-])=O.[K+].[K+].[Cl:18][CH2:19][CH2:20][CH2:21]Br>CC(C)=O>[Cl:18][CH2:19][CH2:20][CH2:21][O:11][C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 53144982,5-Dimethoxyphenol

Product 1

HCID 184672962-(3-Chloropropoxy)-1,4-dimethoxybenzeneYield 86.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2,5-dimethoxyphenol (29 g, 0.19 mol), K2CO3 (35 g), 3-chlorobromopropane (38.5 g, 0.25 mol) and acetone (250 ml) was stirred and refluxed for 6 hours, and then stirred at ambient temperature for 16 hours. The reaction was filtered, and the tiltrate was concentrated to an orange liquid. The liquid was taken up into Et2O, and the organic layer washed with IN NaOH, H2O, dried (MgSO4) and was concentrated to yield 37.8 g of an orange solid. An 11.7 g sample of this solid was flash chromatographed on silica gel (180 g) with 5% EtOAc/CH2Cl2 as eluent. Concentration of similar fractions gave 7.2 g of white, waxy solid, which was recrystallized from petroleum ether to afford a white solid, m.p. 48°-50° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. stirringstirred at ambient temperature for 16 hours
  3. filtrationThe reaction was filtered
  4. concentrationthe tiltrate was concentrated to an orange liquid
  5. washthe organic layer washed with IN NaOH, H2O
  6. dry with materialdried (MgSO4)
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-da21eb0aad764be9828907ea22448b67
Source dataset
uspto-grants-1997_08
Patent number
US05654319

Reaction notes

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