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Reaction of 14 CO 2 with grignard reagents to form either carboxylic acids or ketones. A novel convenient route to [2‐ 14 C] glycerol and [1‐ 14 C] Glycolic acid
Author(s) -
Wirz B.,
Küng W.
Publication year - 1983
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580200510
Subject(s) - chemistry , ether , ketone , bromobenzene , reagent , steric effects , acetone , yield (engineering) , grignard reaction , carboxylic acid , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , materials science , metallurgy
Abstract The reaction of CO 2 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 magnesiumorganic compounds prepared from chloromethyl‐methyl ether, benzyl‐chloromethyl ether and 2‐methoxy‐bromobenzene, upon treatment with CO 2 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.