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Topic: Conversion of Benzene into Naphthalene through EAS  (Read 3350 times)

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Offline Cait

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Conversion of Benzene into Naphthalene through EAS
« on: April 04, 2014, 09:56:39 PM »
     I was wondering if someone could give me some guidance as to how benzene could be converted to naphthalene though an EAS reaction? I know that I can react benzene with succinic anhydride and AlCl3. I can then add SOCl2 and AlCl3 for an acylation reaction.

   These steps would add a second ring with two ketone functional groups to the benzene ring. However, I'm not sure how to create the pi bonds in the second ring. Could 2 mols of NaBH4 be used to convert the two ketones to secondary alcohols and then remove the alcohol groups through dehydration?
   Or could you use Zn(Hg) & HCl to remove the ketone functional groups, add two mols of NBS and then create the double bonds through elimination? Is there another method I missed?

Offline SDVENHI

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Re: Conversion of Benzene into Naphthalene through EAS
« Reply #1 on: April 19, 2014, 03:31:51 AM »
Your approach looks reasonable.  I have seen an anthraquinone reduced to an anthracene with borohydride in refluxing isopropanol.  It is not a big stretch to assume that these conditions would work to convert naphthoquinone into naphthalene.

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