Ethyl Acetate → 1-Phenylcyclobutanecarboxylic acid

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A stirred suspension of palladium on carbon (3.6 g, 5%) in isopropanol (200 mL) was treated in one portion with a solution of ammonium formate (9 g) in water (12.5 mL) followed by a solution of 1-(4-chloro-phenyl)-cyclobutanecarboxylic acid (15 g) in isopropanol (150 mL) also in one portion. The resultant suspension was stirred at 65° C. for 30 minutes and then treated with a further aliquot of a solution of ammonium formate (9 g) in water (12.5 mL). After stirring at 65° C. for a further 4.5 hours the reaction mixture was filtered through Hyflo and the filter pad was washed three times with isopropanol (75 mL). The combined filtrate and washings were evaporated. The solid obtained after standing at room temperature for 3 days was treated with ethyl acetate (350 mL) and water (150 mL) and the organic phase was separated, then dried over magnesium sulfate and then evaporated to give the title compound (9.25 g) as a white solid. LC-MS: RT=3.08 minutes, MS(ES+): very weak 177(M+H)+.

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