Sodium Carbonate → Cyclohexanone, 2-methyl-5-(1-methylethyl)-

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A pressure vessel was charged with 500 g of a mixture of alcohols containing 93.9 g of cis-piperitol, 136.45 g of trans-piperitol, and 187.,8 g of cis and trans-carvenols, 10 g of Girdler G-22 barium promoted copper chromite catalyst, and 10 g of sodium carbonate. The vessel was heated with stirring to 200°-240° C. for 2 hours. After cooling, the product was filtered and distilled to yield 210.5 g of menthone/isomenthone mixture and 147.3 g of carvomenthone. The menthones and carvomenthones were cleanly separated by distillation. The distillation residue containing piperitone and carvenone was hydrogenated at 60 psig hydrogen pressure and ambient temperature using 2% Raney nickel catalyst. Distillation of the hydrogenated product yielded an additional 8.2 g of mentone and 5.3 g of carvomenthone.

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