Potassium Iodide → 4-Allyl-1-(4-Methoxybenzyloxy)Benzene

HRID 703138

Reaction equation

HRID 703138 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.O>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68148ChavicolHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 150074214-Allyl-1-(4-Methoxybenzyloxy)Benzene

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4-Allylphenol, (6.14 g, 0.046 moles), 4-methoxybenzyl chloride, (6.3 ml, 0.046 moles), potassium carbonate (8.3 g, 0.06 moles) and a catalytic amount of potassium iodide were mixed together in about 200 ml acetone, and heated to reflux, with stirring. The reaction was allowed to proceed overnight, then cooled to room temperature and diluted with about 100 ml water. The product was extracted into ethyl acetate (3 times, 300 ml each time), and then dried over magnesium sulfate/potassium carbonate, filtered and concentrated in vacuo to yield the title compound as a light yellow solid, m.p. 59-61° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. extractionThe product was extracted into ethyl acetate (3 times, 300 ml each time)
  4. dry with materialdried over magnesium sulfate/potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-522d4fcc475648378c5d7f4c0f96537b
Source dataset
uspto-grants-1991_01
Patent number
US04981868

Linked notes

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