TRIMETHYLHEPTADIENE DERIVATIVES AND THE MANUFACTURE OF LAVANDULOL AND ITS ESTERS THEREFROM

摘要

1495064 Lavandulol and related compounds BASF AG 4 July 1975 [5 July 1974] 28210/75 Heading C2C Lavendulol (I) (2,6-dimethyl-3-methylol-1,6- heptadiene) or an ester thereof with carboxylic acid RCOOH is prepared from the novel compound 3,5,5-trimethyl-hepta-1,6-dien-3-ol (III) via the known compound 3,5,5-trimethyl-hepta- 2,6-dien-1-ol (IV) or an ester thereof with RCOOH (novel compounds); III may also be converted to I directly. R is H or an aliphatic, cyclo-aliphatic or aromatic radical optionally having substituents that are inert under the reaction conditions, e.g. hydroxy, alkoxy or keto groups. III is converted to IV(a) by treating with an acid catalyst at -50 to + 200‹ C. or by heating in the presence of a catalyst based on a transition metal of sub-group 5 to 7 of the Periodic Table; (b) by reacting with RCOOH or the corresponding anhydride or acid halide in the presence of an acid catalyst, and hydrolysing the resultant ester of IV ; (c) treating with a halogenating agent to obtain 3,5,5-trimethylhepta-2,6-dien-1-yl halide, reacting the halide with an alkali metal, alkaline earth metal or ammonium salt of RCOOH in a non-aqueous medium to obtain an ester of IV and hydrolysing the latter. The ester of IV may be obtained as described above, or by esterifying IV. II or its ester is converted to I or its ester by heating at 150‹-250‹ C. in bulk or in an inert solvent. III may be obtained by reaction of 4,4-dimethyl-5-hexen-2-one with vinyl magnesium chloride, or by ethynylation of the former, followed by partial hydrogenation. Compounds III, IV and esters of IV as well as lavandulol and its esters may be used in perfumery.