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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Sach on November 08, 2017, 09:49:15 AM

Title: Base catalyzed hydrolysis of an ester
Post by: Sach on November 08, 2017, 09:49:15 AM

I want to convert the following molecule (dimethyl 4,4'-(3-(((benzyloxy)carbonyl)amino)thiophene-2,5-diyl)dibenzoate). you can find the molecule in the attachment. I want to hydrolyze the esters and get carboxylic end groups (I put a circle around the esters). I want to use base catalyzed hydrolysis because the protecting group of amine is sensitive to acids. If I hydrolyze the ester using NaOH and heat, I will probably get the 2nd molecule that you can find in the attachment (with ONa end groups).
My question is how can I convert ester to carboxylic acid with adding an acid.
Thank you in advance

Title: Re: Base catalyzed hydrolysis of an ester
Post by: Sach on November 08, 2017, 10:21:04 AM

I already got the answer.

Title: Re: Base catalyzed hydrolysis of an ester
Post by: rolnor on November 08, 2017, 10:31:53 AM

Nice to se that the direct arylation worked Sach. The carbobenzyloxygroup is not acid sensitive, although you can cleave i with strong acid.

Title: Re: Base catalyzed hydrolysis of an ester
Post by: Sach on November 08, 2017, 12:09:56 PM

Thanks, the H-nmr will be done tomorrow and hopefully I will have the desired product.
Fingers crossed