Linalyl chloride

Geraniol is converted into the isomeric alcohol, linalol, hy heat, and both alcohols yield the same chloride when treated wijth dry hydrochloric acid gas. Dupont and Labaune first prepared this chloride, which they considered was linalyl chloride, but Eorster and Cardwell have shown that it is geranyl chloride. 

Synthesis from (3-Pinene. Pyrolysis of /3-pinene yields myrcene, which is converted into a mixture of predominantly geranyl, neryl, and linalyl chloride by addition of hydrogen chloride in the presence of small amounts of catalyst, e.g., copper(I) chloride and an organic quaternary ammonium salt [29]. After removal of the catalyst, the mixture is reacted with sodium acetate in the presence of a nitrogen base (e.g., triethylamine) and converted to geranyl acetate, neryl acetate, and a small amount of linalyl acetate [30]. 

Synthesis from (3-Pinene. For a description of this route, see under Geraniol. Addition of hydrogen chloride to myrcene (obtained from /3-pinene) results in a mixture of geranyl, neryl, and linalyl chlorides. Reaction of this mixture with acetic acid-sodium acetate in the presence of copper(I) chloride gives linalyl acetate in 75-80% yield [37]. Linalool is obtained after saponification. 

Geranyl-neryl chloride Linalyl chloride Scheme 4.2... 

Figure 4.2 Production of geranyl, neryl and linalyl chlorides...

The kinetics of the solvolysis of linalyl p-nitrobenzoate were published in note form 18 years ago, but a full discussion of the reaction, including the mechanism for retention of optical activity in the cyclized products, has now been published as one of the Winstein memorial papers. Another paper on the reaction of linalool with phosphorus pentachloride reports 88 % yield of a ca. 3 1 mixture of geranyl and linalyl chlorides (after 4 h at —10 °C). Acetylation of linalool is notoriously fickle on account of ready rearrangements now a method using t-butyl acetate and sodium methoxide is said to give a 90% yield of the unrearranged acetate. The rearrangements involved in the acid decomposition of the... 

Homolinalyl Acetate.—This body has the constitution CjjHjgOOCCHj, and is prepared by the action of homolinalol-sodium on acetyl chloride, or by tbe action of acetic anhydride on homolinalol. It is an oil with a marked bergamot odour, similar to that of linalyl acetate, but not identical with it. It boils at 111° to 117° at 15 mm. 

That many chemical substances are not soluble in sc carbon dioxide permits selective extraction.100 It is often used with foods, for which it eliminates the possibility of leaving toxic residues of solvents such as methylene chloride. It also avoids the hydrolysis that might occur when esters (for flavors or fragrances) are recovered by steam distillation. It has been used to extract the flavor from hops, the caffeine from coffee, fat and cholesterol from foods,101 pecan oil,102 lavender oil (for which hydrolysis of linalyl acetate could occur in steam distillation), 103 ginseng (from which it does not extract pesticide residues),104 ginger,105 microalgae,106 cooked chicken,107 ethanol from cider,108 and many others. One method used with aromas and con-... 

Lauryl trimethylammonium bromide. See Laurtrimonium bromide Lauryl trimethyl ammonium chloride. See Laurtrimonium chloride Lauryl trimethyl ammonium 2,4,5-trichloro phenoxide. See Laurtrimonium trichlorophenoxide Lautarite. See Calcium iodate Lavamenthe. See Cyclohexylcyclohexanone Lavandex . See Linalyl acetate Lavandin absolute Lavandin benzol absolute. See Lavandin (Lavandula hybrida) oil Lavandin (Lavandula hybrida) oil CAS 8022-15-9 FEMA 2618... 

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