Author Topic: Aldehydes From Ozone  (Read 1439 times)

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Bwiti

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Aldehydes From Ozone
« on: November 06, 2001, 09:19:00 PM »
I know that if ozone is passed through a solution of acetic acid, H2O and isosafrole, piperonal is produced in very good yields(US2916499), but does anyone know for sure if this will work on apiole or myristicin? Peace! 8)

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Rhodium

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Re: Aldehydes From Ozone
« Reply #1 on: November 06, 2001, 09:21:00 PM »
It won't, propenylbenzenes must be used, not allylbenzenes. Isomerize them first.

Bwiti

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Re: Aldehydes From Ozone
« Reply #2 on: November 06, 2001, 09:29:00 PM »
Oops! Remind me to hit myself in the head with a tack hammer -> I meant, would it work on the propenylbenzenes made from apiole or myristicin? I'm asking this, because the patent didn't mention them specifically. It said that compounds with ethylenic groups can be used, but just to be safe, I want to know if anyone's tried this on the above propenylbenzenes in their dreams?

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Rhodium

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Re: Aldehydes From Ozone
« Reply #3 on: November 06, 2001, 09:41:00 PM »
I am sure the reaction would work just as well with those.

Aurelius

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Re: Aldehydes From Ozone
« Reply #4 on: November 08, 2001, 02:46:00 AM »
do they mention the use of zinc in that reaction?

Rhodium

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Re: Aldehydes From Ozone
« Reply #5 on: November 08, 2001, 02:52:00 AM »
They should, as the intermediate ozonide must be reductively cleaved to form the aldehyde.

Bwiti

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Re: Aldehydes From Ozone
« Reply #6 on: November 08, 2001, 09:11:00 AM »
No zinc. It says, "This process requires no reduction step and yields are unexpectedly high.", and everything I've read tells me that no cluster-fuck occurred in the writing of it.
  The patent mentions that other methods that use ozonolysis only give yields of less than 75%, and all of them reqire a reduction. -> That info's on page 1, at the end of paragraph 3. You can find the patent at

http://gb.espacenet.com/


  Good yields and no reduction; not bad for a patent from 1959! 8)

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