wolff_kishner (Stranger)
07-10-04 00:38
No 518451
       Acetals as grignard solvents?     

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
(Chief Bee)
07-10-04 00:50
No 518454
       Dialkoxymethanes/formaldehyde acetals     

Dimethoxymethane and diethoxymethane are both very good solvents for Grignard reactions: http://www.arkat-usa.org/ark/journal/2002/Spinelli/MS-568H/568H.pdf
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    wolff_kishner
(Stranger)
07-10-04 03:35
No 518471
       Why aren't they widely used then?     

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
(Chief Bee)
07-10-04 05:24
No 518482
       price     

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