Fragrance compositions from tertiary terpene alcohols
AssigneeMillennium Specialty Chemicals, Inc.
InventorsBernard J. Kane, Mark B. Erman
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Abstract
Cyclic ethers or chloroketones useful as fragrance components or intermediates are made by reacting a saturated, tertiary terpene alcohol with hypochloric acid under conditions effective to promote oxidation. trans-Pinanol gives predominantly 6,9-dimethyl-7-oxatricyclo[4.3.0.03,9]-nonane, while cis-pinanol yields almost exclusively 1-acetyl-3-(2-chloroethyl)-2,2-dimethylcyclobutane, a new and versatile intermediate for making cyclobutane derivatives having interesting and diverse aromas.
Claims12
A process which comprises reacting a saturated, tertiary terpene alcohol with hypochloric acid under conditions effective to produce at least one oxidation product selected from the group consisting of cyclic ethers, chloroketones, and mixtures thereof.
A composition comprising at least one stereoisomer of 6-chloro-5-(1-methylethyl)-2-heptanone.
A composition comprising at least one stereoisomer of 1-acetyl-3-(2-chloroethyl)-2,2-dimethylcyclobutane.
A cyclobutane having the general structure:
- wherein
- R is a monovalent substituent selected from the group consisting of Me2C(OH)—, MeCO—, CH2═CH—CMe(OH)—, CH2═CMe—, and 2-methyl-1,3-dioxolan-2-yl;
- and
- R′ is a monovalent substituent selected from the group consisting of ClCH2—, Me—, MeOCH2—, EtOCH2—, MeCH(OH)CH2—, Me2C(OH)CH2—, and MeC(O)CH2—
- excluding 1-acetyl-2,2-dimethyl-3-ethylcyclobutane.
Dependencies are inferred from the claim text.