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Topic: 2-phenylethanol -> benzoic acid; why won't these conditions work?  (Read 8927 times)

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Offline nj_bartel

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pocl3 in pyridine to eliminate to styrene, followed by kmno4 to cleave the alkene to benzoic acid

thanks

Offline nielsgeode

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Re: 2-phenylethanol -> benzoic acid; why won't these conditions work?
« Reply #1 on: February 06, 2009, 02:27:30 AM »
pocl3 in pyridine to eliminate to styrene, followed by kmno4 to cleave the alkene to benzoic acid

thanks

Where do you want to eliminate styrene from?  ???

In case you want to make benzoic acid I would choose the following route: bromobenzene + magnesium gives phenylmagnesium bromide. You can react that species with carbon dioxide followed by quenching with water to give benzoic acid :) Seams much easier to me and you avoid using toxic havy metals.

Offline nj_bartel

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Re: 2-phenylethanol -> benzoic acid; why won't these conditions work?
« Reply #2 on: February 06, 2009, 09:39:24 AM »
This is just a theoretical synthesis problem in onlnie homework  :P The styrene was resulting from treatment of the 2-phenylethanol with pocl3.

Offline nj_bartel

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Re: 2-phenylethanol -> benzoic acid; why won't these conditions work?
« Reply #3 on: February 06, 2009, 01:00:14 PM »
NVM, that route would work - just wasn't what the online was looking for (KMnO4 would do it by itself in one step).

Offline macman104

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Re: 2-phenylethanol -> benzoic acid; why won't these conditions work?
« Reply #4 on: February 06, 2009, 05:43:38 PM »
Yes, KMnO4, hot, with concentrated base I believe, will chew away any alkyl group that has a benzylic hydrogen (that would be a hydrogen on the carbon adjacent to the benzene ring), and it will turn it into a carboxylic acid group.

Offline aldoxime_amine

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Re: 2-phenylethanol -> benzoic acid; why won't these conditions work?
« Reply #5 on: February 07, 2009, 10:26:56 AM »
why didn't you dehydrate simply using conc. sulphuric acid?

Offline nj_bartel

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Re: 2-phenylethanol -> benzoic acid; why won't these conditions work?
« Reply #6 on: February 07, 2009, 10:58:37 AM »
Wasn't one of the allowed reactants.

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