From: Paul Handley (p.handley$##$chemistry.uq.edu.au)
Date: Tue Apr 04 2000 - 20:29:38 EDT
>Dear Colleagues:
>I want a simple procedure for the synthesis of c-10 hydroxy Limonene.
>I am aware of the crawfords work (i.e. N-BuLi-Tmedaf-limonene-aireal
>oxydation/reduction procedure/) But we are getting some impurity in this
>process. I would like to know the problems associated with its synthesis
>by any body who has done this reaction. If any body can suggest a more
>convenient method, it is fine.
>I thank you in advance for the information
>Krish
The impurities are a limonene dimer from the air oxidation, and perillyl
alcohol from the deprotonation step. For a more convenient method see US
patent 5574195 Chastain et al. November 12, 1996. Same deprotonation,
react the allyl anion with trimethyl borate, oxidise the adduct with aq.
H2O2. Yield reported is 65-75%, no limonene dimers. I have not tried this
method myself.
I posted this reference previously and I assume you did not receive it, my
apologies if you did.
Good luck,
Paul Handley
Dept. of Chemistry
University of Queensland
Brisbane, Australia
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