Diazomethylation is a fast and reliable way of doing methylations, but with nasty reagents. My lab would need a diazomethylation of a multihydroxylated organic sample, as a reference, but does not have the available permits.
Does anyone know of a commercial source for this procedure?
Hi,
CH2N2 is indeed a very efficient (but nasty) way for methylation. Just a thought: would MeI and K2CO3 be a feasible alternative for your sample?
Works like a charm in anhydrous DMF for my compounds (MeI and DMF are not that nice either, though).
EDIT: Bruce Levison is right. If this organic sample is from kraft lignin or a lignin related substance, Me2SO4 in NaOH would selectively methylate the phenolic hydroxyl groups without side reactions, whereas MeI/K2CO3 would probably be more unselective.
Best regards,
JR
Dimethyl sulfate with base (KOH or NaOH) is what you are looking for, see links below!
http://pubs.rsc.org/en/content/articlepdf/1915/ct/ct9150700008
https://www.chemours.com/Dimethyl_Sulfate/en_US/uses_apps/methylation.html
You could try acid methanolysis - described in the paper at the link below.
You could also try using methanolic boron triflouride although BF3 is not a pleasant chemical either.
Several methods are described in the book "Lipid analysis : a practical approach" (1992) edited by Richard John Hamilton and Shiela Hamilton. The book is quite old but the methods are still applicable.
http://pubs.rsc.org/en/content/articlelanding/2014/ay/c3ay41678j#!divAbstract
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