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

HRID 363656Notes

Reaction equation

HRID 363656 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 filtrate was concentrated to an orange liquid. The liquid was taken up into Et2O, and the organic layer washed with 1N 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 filtrate was concentrated to an orange liquid
  5. washthe organic layer washed with 1N NaOH, H2O
  6. dry with materialdried (MgSO4)
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-b53b796dc2a84394bdd0f2e97286607c
Source dataset
uspto-grants-1999_02
Patent number
US05874435

Reaction notes

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