Carbonation of Grignard reagent

Carbonation of Grignard reagent preparation of carboxylic acids... 

This is an excellent reaction for the conversion of most halides to acids containing one additional carbon atom. Carbonation of Grignard reagents and organoalkali compounds gives acids in yields of 50-85%. Ether solutions of the organometallic compounds formerly were treated with carbon dioxide gas at 10° to -10°. A more recent technique involves pouring the solution onto excess crushed Dry Ice. Carbon dioxide... 

A Hylic rearrangements occur in the carbonation of Grignard reagents from 3-furylmethyl chloride and w-methylbenzyl bromide part of the product in each case contains a nuclear carboxyl group. 

Carbonation of Grignard reagents is similar to the addition of Grignard reagents to aldehydes and ketones. However, in the former reaction, carboxylate is produced, not alcohol. The magnesium carboxylate produced does not dissolve in ethers but when dissolved in acid, carboxylic acids are formed. 

Carbonation of Grignard reagent, 282, 294 Carboxylic acid, conversion to acid chloride, with PCh, 56, 83, 186 with PCh, 41, 209 with SOCh, 258, 283 Chichibabin reaction, 16... 

Solution Carboxylic acids can be prepared by a variety of ways. One can employ direct oxidation with potassium permanganate, KMnOi, or potassium dichromate, K2Cr207, on primary alcohols and aldehydes. KMnOu may also be used to oxidize alkyl substituents on a benzene ring to the carboxyl group. Carboxylic acids can also be prepared by carbonation of Grignard reagents, and hydrolysis of nitriles. 

By carbonation of Grignard reagents. Grignard reagents react with carbon dioxide to yield magnesium carboxylates. Acidification produces carboxylic acids ... 

There are many syntheses of acids where a carbon-carbon bond is formed such as carbonation of Grignard reagents, malonic ester alkylation, and Reformatsky reactions. Some are covered in Chapter 7, and you can review others in your introductory text. 

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