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Topic: How do you synthesise a dialdehyde from cyclopentanone?  (Read 1981 times)

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Offline joyb

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How do you synthesise a dialdehyde from cyclopentanone?
« on: March 07, 2013, 04:22:46 AM »
We're asked how cyclopentanone can be converted to OHCCH2CH2CH2CHO. Any hints where I can find the reactions?
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Offline Hunter2

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Re: How do you synthesise a dialdehyde from cyclopentanone?
« Reply #1 on: March 07, 2013, 05:33:18 AM »
Choose Bayer Villinger Oxidation guides to the Lacton, then hydrolyis to the Hydroxycarbonacid, then reduction to diol or oxidation to dicarbonic acid, then soft reduction to dialdhyde.
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Offline Dan

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Re: How do you synthesise a dialdehyde from cyclopentanone?
« Reply #2 on: March 07, 2013, 06:40:01 AM »
This could be done in two steps.

joyb - you need to break open the ring and form aldehydes, start by thinking about reactions that create aldehydes and break C-C bonds at the same time; a reaction involving oxidation and cleavage.
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