Methyl iodide → HCID 14405960, compound

HRID 1383166Notes

Reaction equation

HRID 1383166 reaction equation
[CH2:1]([C:4]1[C:14]([OH:15])=[C:13]([C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][Br:10])[CH2:2][CH3:3].[C:19](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH2:1]([C:4]1[C:14]([O:15][CH3:19])=[C:13]([C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][Br:10])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanone

Product 1

HCID 14405960HCID 14405960, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.15 g (0.01 mole) of 3-(2-n-propyl-3-hydroxy-4-acetylphenoxy)-1-bromopropane was dissolved in 50 ml of dry acetone. To this solution was added 2.75 g (0.02 mole) of anhydrous potassium carbonate and 3 g (0.02 mole) of methyl iodide. After refluxing for four days under an argon atmosphere, the reaction mixture was filtered and the filtrate concentrated on the rotary evaporator. The residue was chromatographed on silica gel eluting with 2% ethyl acetate/toluene to give 3.1 g (94%) of the title compound as an oil.

Workup

  1. temperatureAfter refluxing for four days under an argon atmosphere
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate concentrated on the rotary evaporator
  4. customThe residue was chromatographed on silica gel eluting with 2% ethyl acetate/toluene

Sources & evidence

ORD record
ord-14b43f25d3da4ecd8cbd97c1d63d4d3a
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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