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Acetals as grignard solvents?

Started by wolff_kishner, July 10, 2004, 12:38:00 AM

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wolff_kishner

Would acetals be acceptable solvents for grignard reactions? In basic conditions, acetals are stable ethers. Since Grignard reactions take place in a basic environment, wouldn't the acetal be indistinguishable from an ether?

I have used the search engine and found nothing either supporting or opposing the use of acetals.

Rhodium

Dimethoxymethane and diethoxymethane are both very good solvents for Grignard reactions:

http://www.arkat-usa.org/ark/journal/2002/Spinelli/MS-568H/568H.pdf




wolff_kishner

Thanks, Rhodium. However, if formaldehyde acetals are good grignard solvents, why aren't they popular? Diethoxymethane would be easy to make and less volatile and dangerous than ethyl ether.

Rhodium

They are more expensive than ether, and in case an acidic workup is made, formaldehyde may contaminate or react with the product.