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Author: Subject: 1,2-Methylenedioxybenzene from Sesamol(4-Hydroxy-1,2-Methylenedioxybenzene). Tosylation and reduction?
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[*] posted on 30-6-2021 at 05:51
1,2-Methylenedioxybenzene from Sesamol(4-Hydroxy-1,2-Methylenedioxybenzene). Tosylation and reduction?


Hello. I was wondering if tosylation of sesamol and reduction with sodium borohydride in ethanol would yield 1,2-Methylenedioxybenzene. I was also thinking zinc dust and heat.


sesamol-533-31-3-_10_81_b_108126 (1).jpg - 6kB




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[*] posted on 30-6-2021 at 06:10


Why not just go for catechol methylenation...? Proven, good yields.
Catechol can be prepared from salicylaldehyde or a hundred different compounds.
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[*] posted on 30-6-2021 at 07:28


Tosylation followed by reduction using NaBH4/NiCl2 would indeed yield benzodioxole.
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[*] posted on 20-7-2021 at 22:49


I would save the Sesamol for something better/more interesting.
Methylation of catechol with DCM works good and catechol is easily purchased.
Link below is a thread about this procedure and in that thread are other links of interest regarding this subject.
http://www.sciencemadness.org/talk/viewthread.php?tid=76069#...
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[*] posted on 21-7-2021 at 06:58


Though the phenolic reduction works, I have to agree from catechol would be a better route. Simply because catechol, sodium, and DCM are so cheap as compared to NaBH4.

Edit:

I.intend to do the synth using the catechol route soon. I have some DCM but not quite enough so I want to get more first.

[Edited on 21-7-2021 by Syn the Sizer]




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[*] posted on 21-7-2021 at 07:06


I have said it before and will say it again. I like smelling thing, never huff, but I waft everything. I want to know what stuff smells like for various reasons. That is actually 1 reason I want some benzenedioxol lol. I know, sounds stupid.



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