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Topic: Synthesis Problem  (Read 2377 times)

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Offline flowerbud5989

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Synthesis Problem
« on: February 07, 2015, 12:18:23 PM »
Does anyone have an idea how to synthesize p-nitropropoxybenzene using only benzene and ispropyl alcohol as carbon sources? I was thinking I would add chlorine to the benzene ring, then use HNO3/H2SO4 to add the nitro group para so that I could do an SnAr reaction using the isopropyl alcohol by first deprotenating it using KOH. I'm stuck here though because I'm not sure how to rearrange the carbons from the isopropyl alchol into a straight chain. Any thoughts? Thanks :)

Offline sjb

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Re: Synthesis Problem
« Reply #1 on: February 07, 2015, 12:40:56 PM »
Does anyone have an idea how to synthesize p-nitropropoxybenzene using only benzene and ispropyl alcohol as carbon sources? I was thinking I would add chlorine to the benzene ring, then use HNO3/H2SO4 to add the nitro group para so that I could do an SnAr reaction using the isopropyl alcohol by first deprotonating it using KOH. I'm stuck here though because I'm not sure how to rearrange the carbons from the isopropyl alchol into a straight chain. Any thoughts? Thanks :)

Well, you can always generate 1-propanol from i-propanol... Also check your pKas, I'm not sure KOH is strong enough a base for what you want.

Offline mjp387

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Re: Synthesis Problem
« Reply #2 on: February 11, 2015, 06:05:04 PM »
Quote
Does anyone have an idea how to synthesize p-nitropropoxybenzene using only benzene and ispropyl alcohol as carbon sources? I was thinking I would add chlorine to the benzene ring, then use HNO3/H2SO4 to add the nitro group para so that I could do an SnAr reaction using the isopropyl alcohol by first deprotenating it using KOH. I'm stuck here though because I'm not sure how to rearrange the carbons from the isopropyl alchol into a straight chain. Any thoughts? Thanks


Well I am not particularly knowledgeable in some of the advanced rearrangement reactions, but you could dehydrate the alcohol, if my memory is correct secondary alcohols are dehydrated at 100C. Then react the alkene it with some hydrogen bromide, in radical conditions. Then substitute it with NaOH, this is my best guess.
I would seriously try adding Iodine to the benzene ring, its a much better leaving group. To do this you should first react the benzene with nitric acid, convert it to the diazonium compound, and react with potassium iodide. There may be another way to make iodo benzene by reacting benzene, iodine, and nitric acid all at the same time.
Now take that propyl alcohol and react it with NaH, forming the salt. My best guess is that it will react with your iodobenzene. Take the product and react it with nitric acid forming your final compound.
Hope this helps.
Mark 
« Last Edit: February 11, 2015, 07:49:25 PM by Arkcon »

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