Pi-tricyclene derivatives and process for preparing pi-tricyclene derivatives
AssigneeInternational Flavors & Fragrances Inc.
InventorsBraja Dulal Mookherjee, Venkatesh Kamath, Edward J. Shuster
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Abstract
A process for the preparation of a mixture of compounds of the structure ##SPC1## Is disclosed whereby a Pi-halotricyclene having the structure ##SPC2## Where Y is chloro, bromo or iodo is reacted with an alkali metal cyanide to prepare the corresponding nitrile; the nitrile is reacted with diisobutylaluminum hyhdride to prepare the corresponding aldehyde, a nortricycloekasantalal which is then condensed with butanone to prepare the above mentioned mixture of compounds. Also claimed are the product ketones which are useful for altering the aroma of consumable products including perfumes, perfume compositions and perfumed articles.
Claims5
A process for preparing a mixture of tricyclic ketones having the structures:
- ##SPC52##
- comprising the steps of:
- i. Reacting a Pi-halotricyclene having the structure:
- ##SPC53##
- with an alkali metal cyanide in the presence of an inert solvent at a temperature in the range of from 80.degree.C up to 100.degree.C, the mole ratio of alkali metal cyanide to pi-halotricyclene being from 10:1 up to 20:1 thereby forming a nitrile having the structure:
- ##SPC54##
- ii. Reacting the thus formed nitrile with diisobutyl aluminum hydride in the presence of an inert solvent, at a temperature in the range of from about 40.degree.C up to 80.degree.C, the mole ratio of diisobutyl aluminum hydride:nitrile being about 1:1, thus forming a nortricycloekasantalal having the structure:
- ##SPC55##
- iii. Reacting the thus formed nortricycloekasantalal with butanone having the structure:
- ##SPC56##
- in the presence of a base selected from the group consisting of an alkali metal hydroxide and an alkaline earth metal hydroxide at a temperature in the range of from 25.degree.C up to 50.degree.C, the mole ratio of butanone:nortricycloekasantalal being in the range of from 5:1 up to 15:1, the weight of butanone as a percentage of reaction mass being from 5% up to 20%, thus forming a tricyclic-alpha, betaunsaturated ketone mixture of compounds which have the structures:
- ##SPC57##
- wherein Y is halogen selected from the group consisting of bromo, chloro and iodo.
A mixture of compounds having the structures:
- ##SPC58##
Dependencies are inferred from the claim text.