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Topic: Synthesis of 3-methoxy,4,5-methylendioxy-allylbenzene  (Read 4998 times)

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Offline limpet chicken

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Synthesis of 3-methoxy,4,5-methylendioxy-allylbenzene
« on: February 03, 2005, 04:11:42 PM »
I am interested in the synthesis of  3-methoxy,4,5-methylendioxy-allylbenzene or myristicin, its an essential oil, found in oil of nutmeg (methoxysafrole)

I am wondering, couldn't it be synthesised from safrole or isosafrole, which is apparently
4,5-methylene-dioxyallylbenzene?

Would methanolic sodium methoxide perhaps add on hte methoxy group at the 3- position?

I wonder, because I require myristicin for a possible experiment with liver cell cultures, and it needs be safrole free, as safrole is metabolised to safrole epoxide, and epoxides are hepatotoxic, and do very nasty things to livers, so I want to synthesize it directly, rather than distil from nutmeg oil itself, where it could be contaminated, as well as avoiding the problem of also introducing elemicin into the mixture.

Thanks.
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Offline Mitch

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Re:Synthesis of 3-methoxy,4,5-methylendioxy-allylbenzene
« Reply #1 on: February 03, 2005, 04:20:00 PM »
The easiest way to do it is to seperate it from nutmeg.
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nocommentes

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Re:Synthesis of 3-methoxy,4,5-methylendioxy-allylbenzene
« Reply #2 on: February 12, 2005, 01:03:12 PM »
Write all structures, maybe ther's a mistake in the name. Than I'll be able to understand what do you mean!

Ishmael46

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Re:Synthesis of 3-methoxy,4,5-methylendioxy-allylbenzene
« Reply #3 on: February 28, 2005, 03:00:43 AM »
With sodium methoxide I'm guessing you'd get a mixture of the 2 and 5 product.  Also, just in case!:

I dont recommend exploring this compound or any of the methamphetamine analogs for recreational use.  There are some horror stories from this exact type of molecule being modified and causing severe brain damage.

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