Question

convert cyclopropane carboxylic acid into cyclopropane methanol​

Answer 1

Cyclopropane derivatives

Cyclopropanes are very weak acids. Their metallation being slow and leading to poor yields of products, they constitute a bench mark to probe the effectiveness of a superbasic reagent. Cyclopropane, when used as a cosolvent, afforded not more than 20% of cyclopropanecarboxylic acid (101) when consecutively treated with pentylsodium/sodium isopropoxide (6.5 h) and carbon dioxide.26 The presence of a phenyl group increases the acidity of cyclopropane and thus renders its metallation easier. Phenylcyclopropane undergoes deprotonation54 on the cyclopropyl ring by Schlosser’s base (LICKOR) or trimethylsilylmethylpotassium in THF to give (1-methylcyclopropyl)benzene (102) in 23% and 33% yield, respectively (Scheme 18). The use of pentylsodium in pentane generates organometallic species resulting from the deprotonation of the aromatic ring.