Carvone - Preparation

Preparation

The dextro-form is obtained practically pure by the fractional distillation of caraway oil; the levo-form from the oils containing it, by first forming its addition compound with hydrogen sulfide, decomposing this by potassium hydroxide in ethanol, and distilling the product in a current of steam. It may be synthetically prepared from limonene nitrosochloride, alcoholic converting this compound into 1-carvoxime, which on boiling with dilute sulfuric acid yields l-carvone. The major use of d-limonene is as a precursor to carvone. The large scale availability of orange rinds, a byproduct in the production of orange juice, has made limonene cheaply available, and synthetic carvone correspondingly inexpensively prepared.

The biosynthesis of carvone is by oxidation of limonene.

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