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Author: Subject: Synthesis of chloromethyl-phenyl ethers

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[*] posted on 3-7-2013 at 12:21
Synthesis of chloromethyl-phenyl ethers

Hi everyone,

I've been wondering that would it be possible to make this synthesis:

I have tried it out not long ago with dicyclohexa-18-crown-6 as a catalyst and a little DMSO to get a better solubility for the potassium-phenolate, but the only thing that I've got from the reaction was diphenoxy-methane, so what chloroether have been produced, it reacted with another phenolate....

I have used this amounts:
5g K-phenolate
100cm3 dichloromethane
20cm3 DMSO
30mg catalyst

The reaction mixture have been refluxed for 5 hours.

Anyone has any idea that how to make this compound?

I am also making a paralell reaction without DMSO and without reflux.

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[*] posted on 4-7-2013 at 14:20

Generally it is not possible to obtain a product that is several magnitudes more electrophilic that the starting material by a simple alkylation for it reacts further with the nucleophile much more readily.

If you want to prepare PhOCH2Cl from phenol and CH2Cl2, there is a two step synthesis described in Chemische Berichte 1963, 96, 2266-2280. Of course, there are a few other ways, if you are willing to use other starting materials.

…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)

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