Author Topic: Acetals as grignard solvents?  (Read 3087 times)

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wolff_kishner

  • Guest
Acetals as grignard solvents?
« on: July 10, 2004, 12:38:00 AM »
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

  • Guest
Dialkoxymethanes/formaldehyde acetals
« Reply #1 on: July 10, 2004, 12:50:00 AM »
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

  • Guest
Why aren't they widely used then?
« Reply #2 on: July 10, 2004, 03:35:00 AM »
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

  • Guest
price
« Reply #3 on: July 10, 2004, 05:24:00 AM »
They are more expensive than ether, and in case an acidic workup is made, formaldehyde may contaminate or react with the product.