[CHM]

Hi
I want to react 2-Cl-C6H4-COO-C6H5-N=N-C6H5 + R-OH to give ether  derivative. but hydrolysis for ester to alchol was happen.the conditions that I make are solvent is aceton, potassium carbonate anhydrous and refluxe under nitrogen for 24h, what can i do to mak ether with keep the ester side.
thanks

[HP]

You should react your Cl-ester with preliminary prepared Me-alcoholat to do the Williamson synthesis best for example:
R-OH + Na --> R-O:-Na+

[CHM]

Did you mean that R-ONa prepared then dropwise to Cl-ester and reaflux so NaCl will formed and no effect for ester bond by use Williamson synthesis ?

[HP]

Did you mean that R-ONa prepared then dropwise to Cl-ester and reaflux so NaCl will formed and no effect for ester bond by use Williamson synthesis ?

Indeed and stoichiometrically

[CHM]

I read about Williamson synthesis be SN2 reaction but my compound is chlorobenzen ester and the subestitution will be not in Williamson synthesis.do you have another idea? thanks

[HP]

You are right. Sorry i didnt see your compond is aromatic halide..so  it wont react easily with the alcoxide The counter case - reaction of alkaly phenolates with alkyl halides is possible but every direct transformation of your aryl halide to phenol is risky about ester hydrolysis...What about reaction your chloroaryl compound with NaNH2 to the coresponding p-aminobenzoic ester derivate? After that using chemistry of amines - diazotation with NaNO2/H2SO4 to diazonium salt which i think could directly react with alcohols to the coresp aryl ether.