Quote: | So instead i will react benzhydryl with ethylene glycol in methylbenzene with conc H2SO4 as the catalyst. This should give me the benzhydryl
2-hydroxyethyl ether. |
Hmm... for someone who only a couple of days ago never even heard about SN1 nucleophilic substitutions on benzhydryl alcohols, you became quite over
ambitious. How about explaining what role would toluene have and why do you think having a biphasic toluene/ethylene glycol system is going to help (I
don't think these two solvents are miscible). I can only see negative aspects: temperature limited by the toluene reflux, benzhydryl alcohol
preferentially partitioning in the toluene phase and H2SO4 in the glycol phase, etc.
Maybe you could first explain what was it that you found impractical in the procedure from JACS? I really can't see how more simple you could have
it. If you don't have any tosylic acid, then try with a similar equivalent of NaHSO4, H2SO4, H3PO4 or any other non-nucleophilic strong enough acid
and follow with TLC (the reaction rate will change if you use a different acid catalyst!). If the reaction rate gets too slow due to the catalyst
exchange, then add some more or heat up by 20°C or so.
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