Synthesis of acyclic, terpene alcohols
AssigneeSCM Corporation
InventorsRalph E. Close, John M. Derfer
Life of this patent
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Abstract
Shown is a process for the synthesis of acyclic, terpene alcohols, such as 3,7-dimethyloctan-1-o1 and 7-substituted hydroxy or ethoxy derivatives thereof, wherein 3-methylbut-1-yn or the 3-substituted hydroxy or ether derivative thereof is coupled with a C.sub.5 coupling reagent having the configuration ##STR1## X being a leaving group such as chloride, bromide, iodide, tosylate and mesylate; R being ##STR2## or OR', R' being a lower alkyl up to 5 carbon atoms, phenyl, substituted phenyl up to 10 carbon atoms, cycloalkyl or aralkyl up to 10 carbon atoms, followed by hydrogenation and saponification or deetherification.
Claims8
A process for the preparation of 3,7-dimethyloctan-1-ol and derivatives thereof substituted at the 7-position with an hydroxy or ether group, comprising the steps of
- a. coupling 3-methylbut-1-yn or the 3-hydroxy or ether substituted derivative thereof with a C.sub.5 coupling reagent having the configuration ##STR10## X being a leaving group selected from the group consisting of chloride, bromide, iodide, tosylate and mesylate, R being ##STR11## or OR', R' being a lower alkyl up to 5 carbon atoms, phenyl, substituted phenyl up to 10 carbon atoms, aralkyl up to 10 carbon atoms or cycloalkyl up to 10 carbon atoms;
- b. said coupling being carried out in the presence of a cuprous salt and an acid scavenger;
- c. subjecting the reaction product of step a,b) to hydrogenation and saponification or ether cleavage to convert the ester or ether group in the 1-position to an hydroxyl group.
A process for the preparation of hydroxycitronellol comprising
- a. coupling 1-chloro-4-acetoxy-2-methyl-2-butene with 3-methylbut-1-yn-3-ol in the presence of cuprous halide, a hydrogen halide acceptor and a non-aqueous medium;
- and
- b. subjecting the reaction product of step (a) to hydrogenation and saponification.
A process for the preparation of hydroxycitronellol comprising
- a. reacting 3-methylbut-1-yn-3-ol with cuprous halide in saturated aqueous ammonium chloride to obtain the methylbutynol copper derivative which is isolated;
- b. reacting the methylbutynol copper derivative of step (a) with 1-chloro-4-acetoxy-2-methyl-2-butene in a non-aqueous medium;
- and
- c. subjecting the reaction product of step (b) to hydrogenation and saponification.
Dependencies are inferred from the claim text.