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Topic: Decarboxylation of aspirine to phenyl acetate  (Read 3341 times)

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Offline Phenyl

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Decarboxylation of aspirine to phenyl acetate
« on: December 26, 2012, 04:06:40 PM »
Hey guys.

The wikipedia article of phenyl acetate, http://en.wikipedia.org/wiki/Phenyl_acetate, says that phenyl acetate can be made into phenol and sodium acetate by adding sodium hydroxide.

It also says that aspirine can be decarboxylated into phenyl acetate, how is that done? I can't find anything about it.

Offline Hunter2

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Re: Decarboxylation of aspirine to phenyl acetate
« Reply #1 on: December 27, 2012, 04:30:18 AM »
Only heat.

Offline Phenyl

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Re: Decarboxylation of aspirine to phenyl acetate
« Reply #2 on: December 27, 2012, 05:44:52 PM »
Only heat.

Wouldnt that just result in salicylic acid and acetic acid?

Offline Hunter2

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Re: Decarboxylation of aspirine to phenyl acetate
« Reply #3 on: December 28, 2012, 03:28:56 AM »
For this you need water to crack the ester. There is normaly no water, if you heat it.

Offline Pranav

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Re: Decarboxylation of aspirine to phenyl acetate
« Reply #4 on: December 28, 2012, 03:32:24 AM »
Only heat.

Wouldnt that just result in salicylic acid and acetic acid?

How do you get that?
Did you check out Decarboxylation of Aromatic Acids somewhere?
Decarboxylation of aromatic acids is generally carried out by heating with copper and quinoline.

Offline Hunter2

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Re: Decarboxylation of aspirine to phenyl acetate
« Reply #5 on: December 28, 2012, 03:33:53 AM »
Even better if you add an catalyst.

Offline Pranav

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Re: Decarboxylation of aspirine to phenyl acetate
« Reply #6 on: December 28, 2012, 03:36:31 AM »
Even better if you add an catalyst.

Or use cuprous oxide instead of copper. :)

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