Eco-friendly synthesis of β-nitro ketones

19 Aug 2011

A variety of β-nitro ketones have been synthesised at room temperature using a supported nitrite.

Scientists from Italy have developed a more eco-friendly route to synthesize β-nitro ketones. Nitroalkanes are an important class of organic substrates as the nitro group can be converted into many other functionalities, which makes them key starting materials for many fine chemicals. Currently, the main method to make these compounds is by a Miyakoshi procedure – however, the method is limited to simple α,β-unsaturated ketone starting materials, gives only moderate yields and requires the presence of volatile organic solvents.

However, in this work, β-nitro ketones could be synthesized from a variety of α,β-unsaturated ketones using a solid supported nitrite, acetic acid and cyclopentyl methyl ether (CPME), an emerging ‘green solvent’. This method works well with complex starting materials and it is able to preserve other functionalities, thereby minimizing work-up procedures (simple filtration and evapouration of the acetic acid and solvent) and decreasing the E-factor.