I am doing a hydroboration-protonation reaction using dicyclohexylborane to reduce a triple bond to a cis-double bond. I use acetic acid, followed by sodium hydroxide and hydrogen peroxide in my workup. Cyclohexanol is formed as a byproduct and does not get separated after extraction. My product is soluble in all organic solvents including hexane. Could someone please tell me how to remove cyclohexanol from my product?
Dear Madhur S Joshi, this certainly depends on whether your product is a solid or a liquid. If it's a liquid, you could try to remove the cyclohexanol by vacuum distillation. Another option would be to crystallize your product from acetonitrile. In our hands, this particular solvents sometimes worked really well with compounds that are highly soluble in hexane. You could also consider extracting the cyclohexanol with water, in which it is significantly soluble (ca. 40-60 g/L).
Hi Madhur S Joshi, I fully agree with Packiaraj Jeyachandran Manohari in that fractional distillation is perhaps the best way to remove the cyclohexanol by-product. Of course, the success of this method depends on the difference in boiling points between your main product and the cyclohexanol.
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