Myrcene impurities

Linalool can also be made along with nerol and geraniol via the hydrochlorination of myrcene. After conversion of the chlorides to acetates followed by saponification of the acetates, the mixture of alcohols is obtained. Fractionation of the mixture gives linalool in about 95% purity, but the presence of close boiling impurities prohibits manufacture of a perfiimery-quahty product. 

The terpenes used were mainly /3-pinene fractions provided by DRT (Soci6td des Derives Rdsiniques et Terpeniques, Vielle-S Girons) and, for certain experiments a turpentine oil containing the main three terpenes a-pinene, /3-pinene, and A -carene. The /3-pinene fractions contained 80-90% /3-pinene, 2% a-pinene, 4-5% myrcene, 2-3% dipentene and 700-1500 ppm S. GC-MS analyses showed that sulfur impurities were composed of alkyl and alkenyl sulfides (mainly dimethyl sulfide), alkyl and alkenyl disulfides (mainly dimethyl disulfide), trisulfides, thiophene and alkylthiophenes (methyl, dimethyl, acetyl and tertiobutyl). 

But it is not this step that makes the synthesis remarkable, but rather Takasago s route focitronel lal. Pinene is another terpene that is produced in only low enantiomeric excess by pine trees (and indeed, which is the major enantiomer depends on whether it is a European or a North Americar pine tree). But in the menthol process none of this matters, and cheap, enantiomerically impure pinene can be used, because the first step is to convert it to an achiral terpene, myrcene. Lithium diethylamide adds to this diene to give an allylic amine. 

The block copolymers were obtained in relatively low yields (88-917o). This is due at least in part to the presence in myrcene of ca. 107o of impurities, which are not polymerized. Excluding this... 

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