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Chemistry Forums for Students => Undergraduate General Chemistry Forum => Topic started by: indietro on January 23, 2010, 07:36:59 PM

Title: deprotonation of an alcohol
Post by: indietro on January 23, 2010, 07:36:59 PM

i was wondering if NaH is able to deprotonate an alcohol. I've included the compound that contains the alcohol i want to deprotonate. (I want to deprotonate it so that I can add an alkyl halide to make an ether) thanks in advance :)

Title: Re: deprotonation of an alcohol
Post by: stewie griffin on January 23, 2010, 08:38:48 PM

NaH will definitely deprotonate alcohols. I do it all the time when I protect as a benzyl group using NaH and BnBr.
I use NaH in THF.

Title: Re: deprotonation of an alcohol
Post by: indietro on January 23, 2010, 08:56:12 PM

so since there is a benzene with a substituent should I use Na-H in THF as you suggest, to protect the ring?