Reaction of 14CO2 with grignard reagents to form either carboxylic acids or ketones. A novel convenient route to [2-14C] glycerol and [1-14C] Glycolic acid
✍ Scribed by B. Wirz; W. Küng
- Publisher
- John Wiley and Sons
- Year
- 1983
- Tongue
- French
- Weight
- 493 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
The reaction of C02 with GRIGNARD reagents carrying an ether grouping in a sterically suitable position can be directed to afford predominantly either the carboxylic acid or the symmetrical ketone. Thus, the magnesiumorqanic compounds prepared from chloromethyl-methyl ether, benzyl-chloromethyl ether and 2-methoxy-bromobenzene, upon treatment with C02 under appropriate conditions give the corresponding ketones in excellent yield. An attempt is made to rationalize this finding from a mechanistic viewpoint. The easily accessible 1,3-bis(benzyloxy)acetone represents a convenient intermediate for an efficient and simple synthesis of glycerol.