70286-31-6Relevant academic research and scientific papers
Heteropoly acid catalyzed cyclization of nerolidol and farnesol: Synthesis of α-bisabolol
De Meireles, Augusto L.P.,Costa, Maíra Dos Santos,Da Silva Rocha, Kelly A.,Gusevskaya, Elena V.
, p. 271 - 275 (2015/07/07)
Heteropoly acid H3PW12O40 is an active and environmentally friendly homogeneous catalyst for the synthesis of α-bisabolol, a high-priced and highly demanded ingredient for the fragrance, cosmetic and pharmaceutical industries, starting from more abundant biomass-based sesquiterpenic alcohols. The solvent nature remarkably affects the reaction pathways and product selectivity. In acetone solutions, α-bisabolol can be obtained in 55-60% GC yields from nerolidol and 60-70% GC yields from farnesol at complete substrate conversions, which are probably the best results ever reported for these reactions. α-Bisabolol synthesized by this method contains no farnesol, which is a potentially allergenic compound and should be avoided in the commercially used α-bisabolol. This advantage is especially important because the distillative separation of α-bisabolol and farnesol is a troublesome task. The catalyst shows high turnover numbers and operates under mild nearly ambient conditions.
PROCESS FOR REMOVING FARNESOL FROM MIXTURES WITH ALPHA-BISABOLOL
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Page/Page column 5, (2008/06/13)
Process for esterification of farnesol in an initial mixture comprising alpha-bisabolol, farnesol and optionally other components, with the following steps: 1. Preparation or production of the initial mixture, 2. Adding (i) a transesterification catalyst and (ii) one or more compounds of formula (B) [in-line-formulae]R2YnCO2R1??(B) [/in-line-formulae] in which the following applies: R1 stands for an alkyl residue with 1 to 12 C atoms; R2 stands for hydrogen, an alkyl residue with 1 to 20 C atoms, a cycloalkyl residue with 5 to 20 C atoms, an aryl residue with 6 to 20 C atoms or a heteroaryl residue with 5 to 20 C atoms; and Y stands for CH2, CH(Me), CH(Et), C(Me)2, CH2—CH(Me), CH(Me)-CH2 or CH2—CH(Me)-CH2 and n stands for a whole number from 0 to 6; or R2 stands for a group CO2R3, R3 standing for an alkyl residue with 1 to 12 C atoms; and Y stands for CH2, CH(Me), CH(Et), C(Me)2, CH2—CH(Me), CH(Me)-CH2 or CH2—CH(Me)-CH2 and n stands for a whole number from 0 to 8, or Y stands for an optionally substituted phenyl or naphthyl ring with a total of at most four substituents on the ring, n=1 applying.
CYCLIZATION OF SOME LINEAR TERPENOLS INITIATED BY "ACTIVATED" DMSO
Surkova, A. A.,Lozanova, A. V.,Dragan, V. A.,Gur'yan, V. A.,Moiseenkov, A. M.
, p. 760 - 762 (2007/10/02)
It was shown that the acylhydroxysulfonium salt generated in situ from DMSO and trifluoroacetic anhydride causes low-temperature cyclization of geraniol, linalool, and nerol in an aprotic medium to a mixture of p-menthane monoterpenoids, and the maximum yield is obtained in the case of the last two terpenols.A similar result was obtained for E-nerolidol.
Effect of Substituent on Reactions Remote from Silicon: Regioselective α-Alkylation of α-Silylallyl Carbanions
Horvath, Raymond F.,Chan, Tak Hang
, p. 317 - 327 (2007/10/02)
α-Silylallyl carbanions having metal-ion complexing substituents on silicon react with alkyl halides to give α-substituted allylsilanes regioselectively.The extent of α-selection depends significantly on the nature of the ligand and solvent.The synthetic utility of these systems is demonstrated by application in the synthesis of α-(E)-bisabolene.
A New Method for C-C Coupling of Terminal Alkenes via a Sulphonylation-Alkylation-Desulphinylation Sequence: Synthesis of E- and Z-α-Bisabolenes
Baldwin, Jack E.,Adlington, Robert M.,Ichikawa, Yoshiyasu,Kneale, Christopher J.
, p. 702 - 704 (2007/10/02)
A new method for regiospecific C-C coupling of terminal alkenes based on a sulphonylation-alkylation-desulphinylation process, mediated through allylic sulphinic acids, and its application to the conversion of limonene into E- and Z-α-bisabolenes, are described.
