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ADDkid
04-10-04 15:07
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<a href="https://www.the-hive.ws/forum/showflat.pl?Number=500045&page=28&view=&sb=&Search=&vc=&new=&start=0&xrated=y&&URLForums=" title="Click here to show this downrated post">P2P from benzyl alcohol and ethanal one pot?</a>
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<i title="This post has been downrated by the moderators">(Rated as: insignificant)</i>
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Kinetic<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">04-10-04 16:41</span><br>
<span title="Link to this post by using the markup [500060]">No 500060</span><br>
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<b title="The subject of this post">Pretty insignificant</b>
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Although - unlikely as it seems, you <i>may</i> be onto something here.<br><br>There is a catch, of course.<br><br>The closest thing I can find to your proposal is a reference in which benzyl alcohol, acetaldehyde (ethanal) and methanol are reacted together, and undergo the following reaction. The product is 1-methoxy-1-phenyl-2-propanol:<br><center><br><span title="Molecular formula of "><br><applet codebase="./includes/marvin" archive="marvin.jar" code="MView" width="350" height="200"><br><param name="mol" value="c1ccccc1CO.CC(=O).CO>>c1ccccc1C(OC)C(O)C"><br><param name="preload" value="MolExport,Parity"><br><param name="background" value="#f5f5f5"><br><param name="molbg" value="#f5f5f5"><br><param name="implicitH" value="hetero"><br><param name="navmode" value="rot3d"><br></applet><br></span><br><a href="https://www.the-hive.ws/forum/faq.pl?Cat=#applet" title="You have to enable Java in order to see the formula. Jump to the FAQ for an explanation.">Molecule:</a> ("c1ccccc1CO.CC(=O).CO>>c1ccccc1C(<wbr>OC)C(O)C<wbr>")<br></center><br>Epoxides, diols, O-acetylated diols, and probably O-alkylated diols can be isomerised to P2Ps with sulfuric acid. However the abstract of the article for this transformation makes reference to chromium tricarbonyl, which makes an otherwise very interesting idea much less so.<br><br>Still, the reference is:<br><br><b>Elaboration of <i>alpha</i>-substituted benzyl ethers and sulphides by suppression of the Wittig and related rearrangements</b><br><i>Stephen G. Davies, Nicholas J. Holman, Charles A. Laughton, Bryan E. Mobbs</i><br>J. Chem. Soc., Chem. Commun., 1983<br><i>[No DOI found]</i><br><br><b>Abstract</b><br><br>Co-ordination of benzyl alkyl ethers and sulphides to chromium tricarbonyl allows a-substitution via the corresponding a-carbanions to be achieved by suppression of the Wittig and related rearrangements.<br><br><br>If it did turn out to be a viable route, it would be quite an elegant pathway to meth, via oxidation of the alcohol (the other one is protected as an ether; Jones reagent seems selective for this) to the O-methyl phenylacetylcarbinol (O-methyl d,l-PAC), followed by standard reductive amination. An HI reduction would remove the -OMe, instead of the usual -OH, giving methamphetamine. See <span title="Jump to this post"><a href="../DUMMY">Post 344446</a> <i>(Rhodium: "Hypophosphorous acid¯iodine: a novel reducing ...", Stimulants)</i></span> for an example in which -OMe is reduced by an HI-based system.
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