I am looking for a way of converting a hydroxyl group into a carboxyl group in an aqueous environment for eventual coupling to an amine. There seem to be plenty of ways of achieving this in various solvent e.g. using succinic anhydride (see below scheme for mPEG)

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Would the above reaction using succinic anhydride form a stable carboxyl group if the reaction was done in water?

Or should I take a different approach, oxidising the -OH group using Potassium permanganate in a basic aqueous environment, as described here:


  • 1
    $\begingroup$ Water is about as good a nucleophile as the -OH group of mPEG so I think attempting the reaction with succinic anhydride in an aqueous environment is unlikely to work. Do you have to do this in aqueous? $\endgroup$
    – Waylander
    Commented May 26, 2022 at 9:02
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    $\begingroup$ There is a good procedure in water/acetonitrile here orgsyn.org/demo.aspx?prep=v81p0195 $\endgroup$
    – Waylander
    Commented May 26, 2022 at 9:06


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