Tosylates an option for Reducing OH groups to Hydrocarbons

java · Consumer

"An alternative to halogenation is putting a protecting group on the alcohol that will make it a good leaving group. For example, p-toluenesulfonyl chloride will react with the alcohol to form what is called the tosylate. This can then be removed reductively with strong reducing agents like Et3BH or LiAlH4," wrote Movies, somewhere in the chemistry forum's. However as attractive as it may appear the reducing agent, and the tosylating agents need to include some OTC agents for the hobby'st to make or aquire without rising red flags.

So I will try to start a list of OTC reducing and tosylating agents to make this a more attractive method, so your addition is welcomed ........java

fcknut · Mon Aug 22, 2005 4:41 am

ok, just realised that i've posted something in the halogenation thread about this subject but i'll put it here also.

a very nice tosyaltion procedure is reporte by tanabe et al (tenabe) in 1999 but i can't remember the journal name...

it uses catalytic methylamine hcl and stoichiometric ethylamine (i think) so i'm not sure how 'otc' this is... but it is neat and works well. essentially it relies on the slight difference in basicity between the two amines in order to allow use of methylamine (free) as a nucleophilic catalyst.