Sciencemadness Discussion Board

NaOH as substitute for KOH in methylation of amino alcohols

itsmetheuglykid - 20-2-2015 at 11:18

Reference: http://pubs.acs.org/doi/pdf/10.1021/jo01067a619

Does anyone know why NaOH would not be ideal to use in stratification step in substitute of KOH? Specifically the methylation 1-amino-2-propanol. I know that NaOH is more hygroscopic than it's buddy, probably helping keep moisture levels lower in the final product. I would prefer not to have to wait a week for KOH to come in the mail. (no soap making shops where i live)

[Edited on 20-2-2015 by itsmetheuglykid]

Crowfjord - 20-2-2015 at 11:46

In your reference, they use NaOH in one example, and KOH in another. They are just used as base in the workups. Moisture absorbance or solubility might have played a role in their choice, but I doubt there would be much difference exchanging one for the other in this particular instance.

chemrox - 20-2-2015 at 15:20

I always used KOH for adding solid (flakes) of base. It seems to be easier to visualize the response using KOH rather than with NaOH but I was following procedures and wondered about it from time to time. For those who would like to read the whole article:

Attachment: ACS-N-Me_ation of amino alcohols and mercaptans.pdf (237kB)
This file has been downloaded 363 times


itsmetheuglykid - 24-2-2015 at 07:31

Ya it worked out just fine...thanks.

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