Sciencemadness Discussion Board - Synthesis of chloromethyl-phenyl ethers

Synthesis of chloromethyl-phenyl ethers

LiD - 3-7-2013 at 12:21

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.

Thanks!

Nicodem - 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.