2-tert-Butyl-4-methylphenol → Cyclohexanol, 2-(1,1-dimethylethyl)-4-methyl-

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Reaction Steps

A mixture of 400 g (2.44 moles) of 2-tert-butyl-4-methylphenol, 400 ml of dioxane and 1 g of ruthenium hydroxide was initially taken in an autoclave and hydrogenated at 120° C. and under a hydrogen pressure of 50 bar until the pressure remained constant (total hydrogenation time about 3 1/2 hours). The catalyst was separated off, after which the dioxane was distilled off and the residue was fractionated under 0.01 mbar. After a small initial fraction (15 g with a boiling point up to 60° C./0.01 mbar), 401 g (2.36 moles, corresponding to a yield of 96%) of 2-tert-butyl-4-methylcyclohexanol distilled over at 80°-85° C./0.01 mbar and, after cooling, solidified to a semisolid mass. On the basis of 13C NMR spectroscopic data, the product was identified as a diastereomer mixture of the following composition: A:B:C:D=68:29:2:1 ##STR7##

Provenance & Evidence