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Topic: Aspirin  (Read 4493 times)

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Offline Super Newb

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Aspirin
« on: August 26, 2012, 11:10:07 AM »
I am wondering if the sequence of oxidation or acylation will affect the overall synthesis. Any help will be appreciated :D
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Offline discodermolide

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Re: Aspirin
« Reply #1 on: August 26, 2012, 11:12:17 AM »
Quote from: Super Newb on August 26, 2012, 11:10:07 AM
I am wondering if the sequence of oxidation or acylation will affect the overall synthesis. Any help will be appreciated :D

I don't think your structures are correct!
You cannot acylate a methyl group with acetic anhydride/acetic acid.
The structure you drew is not aspirin which is acetyl salicylic acid
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Offline rrr_asd

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Re: Aspirin
« Reply #2 on: August 26, 2012, 06:10:20 PM »
I think, it's must be correct.
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Offline OC pro

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Re: Aspirin
« Reply #3 on: August 27, 2012, 02:34:39 AM »
The first step will not work.
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Offline IsotopeBill

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Re: Aspirin
« Reply #4 on: August 27, 2012, 05:44:05 PM »
Do you have to start with phenol?  If so, look into ortho lithiation followed by treatment with an electrophile.
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Offline Super Newb

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Re: Aspirin
« Reply #5 on: August 28, 2012, 06:24:43 AM »
Quote from: OC pro on August 27, 2012, 02:34:39 AM
The first step will not work.

It is similar to the logic that aniline cannot be acylated and alkyalated by AlCl3 ? Much Thanks :D
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Offline discodermolide

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Re: Aspirin
« Reply #6 on: August 28, 2012, 08:19:22 AM »
Quote from: Super Newb on August 28, 2012, 06:24:43 AM
Quote from: OC pro on August 27, 2012, 02:34:39 AM
The first step will not work.

It is similar to the logic that aniline cannot be acylated and alkyalated by AlCl3 ? Much Thanks :D

The phenol will react!
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Offline Super Newb

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Re: Aspirin
« Reply #7 on: August 28, 2012, 08:44:58 AM »
Quote from: discodermolide on August 26, 2012, 11:12:17 AM
Quote from: Super Newb on August 26, 2012, 11:10:07 AM
I am wondering if the sequence of oxidation or acylation will affect the overall synthesis. Any help will be appreciated :D

I don't think your structures are correct!
You cannot acylate a methyl group with acetic anhydride/acetic acid.
The structure you drew is not aspirin which is acetyl salicylic acid

I don't get what you mean by the the structure is wrong (isn't acetylsalicylic acid the same as aspirin)?

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Offline curiouscat

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Re: Aspirin
« Reply #8 on: August 28, 2012, 08:56:32 AM »
Quote
I don't get what you mean by the the structure is wrong (isn't acetylsalicylic acid the same as aspirin)?

The acetyl group you drew originally looks wrong.
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Offline discodermolide

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Re: Aspirin
« Reply #9 on: August 28, 2012, 09:00:56 AM »
Quote from: Super Newb on August 28, 2012, 08:44:58 AM
Quote from: discodermolide on August 26, 2012, 11:12:17 AM
Quote from: Super Newb on August 26, 2012, 11:10:07 AM
I am wondering if the sequence of oxidation or acylation will affect the overall synthesis. Any help will be appreciated :D

I don't think your structures are correct!
You cannot acylate a methyl group with acetic anhydride/acetic acid.
The structure you drew is not aspirin which is acetyl salicylic acid

I don't get what you mean by the the structure is wrong (isn't acetylsalicylic acid the same as aspirin)?



Check your structures they are incorrect.
You drew 2-(acetoxymethyl)benzoic acid not acetylsalicylic acid!
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