Tricyclo-.alpha.,.beta.-unsaturated aldehyde
AssigneeKao Soap Co., Ltd.
InventorsNaotake Takaishi, Yoshiaki Inamoto, Masamoto Matsukane
Life of this patent
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Abstract
A tricyclo-.alpha.,.beta.-unsaturated aldehyde represented by the formula (I), ##STR1## wherein the group ##STR2## is attached to the exo side of the norbornane ring at the 8- or 9-position, R represents an alkyl group having 1 to 6 carbon atoms, and the dotted line between carbon 3 and carbon 4 represents a saturated or ethylenically unsaturated bond possesses odorous characteristics and is useful for perfume compositions.
Claims11
An endo-tricyclo-.alpha.,.beta.-unsaturated aldehyde represented by the formula (I), ##STR9## wherein the group ##STR10## is attached to the exo side of the norbornane ring at the 8- or 9-position, R represents an alkyl group having 1 to 6 carbon atoms, and the dotted line between carbon 3 and carbon 4 represents a saturated or ethylenically unsaturated bond.
A process for producing an endo-tricyclo-.alpha.,.beta.-unsaturated aldehyde represented by the formula (I), ##STR11## wherein the group ##STR12## is attached to the exo side of the norbornane ring at the 8- or 9-position, R represents an alkyl group having 1 to 6 carbon atoms, and the dotted line between carbon 3 and carbon 4 represents a saturated or ethylenically unsaturated bond, which comprises reacting 8- or 9-exo-formyl-endo-tricyclo[5.2.1.0.sup.2,6 ]deca-3-ene or 8-exo-formyl-endo-tricyclo[5.2.1.0.sup.2,6 ]decane represented by the formula (III), ##STR13## wherein the group OHC-- is attached to the exo side of the norbornane ring at the 8- or 9-position, and the dotted line between carbon 3 and carbon 4 represents a saturated or ethylenically unsaturated bond, or a mixture thereof, with an aliphatic aldehyde represented by the formula (IV),
- R--CH.sub.2 CHO (IV)
- wherein R is the same as defined above.
A process for producing a tricyclo-.alpha.,.beta.-unsaturated aldehyde represented by the formula (V), ##STR14## wherein the group ##STR15## is attached to the exo side of the norbornane ring at the 8- or 9-position, and R represents an alkyl group having 1 to 6 carbon atoms, which process comprises:
- (a) reacting endo-dicyclopentadiene with carbon monoxide and hydrogen in the presence of a rhodiumtriarylphosphine catalyst to obtain 8- or 9-exo-formyl-endo-tricyclo[5.2.1.0.sup.2,6 ]deca-3-ene, and
- (b) condensing said 8- or 9-exo-formyl-endo-tricyclo[5.2.1.0.sup.2,6 ]deca-3-ene with an aliphatic aldehyde represented by the formula (IV),
- R--CH.sub.2 CHO (IV)
- wherein R is the same as defined above.
A process for producing a endo-tricyclo-.alpha.,.beta.-unsaturated aldehyde represented by the formula (VI), ##STR16## wherein the group ##STR17## is attached to the exo side of the norbornane ring at the 8-position, and R represents an alkyl group having 1 to 6 carbon atoms, which process comprises:
- (a) reacting endo-dicyclopentadiene with carbon monoxide and hydrogen in the presence of a rhodiumtriarylphosphine catalyst to obtain 8- or 9-exo-formyl-endo-tricyclo[5.2.1.0.sup.2,6 ]deca-3-ene,
- (b) hydrogenating said 8- or 9-exo-formyl-endo-tricyclo[5.2.1.0.sup.2,6 ]deca-3-ene in the presence a hydrogenation catalyst to obtain 8-exo-formyl-endo-tricyclo[5.2.1.0.sup.2,6 ]decane, and
- (c) condensing said 8-exo-formyl-endo-tricyclo[5.2.1.0.sup.2,6 ]decane with an aliphatic aldehyde represented by the formula (IV),
- R--CH.sub.2 CHO (IV)
- wherein R is the same as defined above.
A perfume composition comprising an endo-tricyclo-.alpha.,.beta.-unsaturated aldehyde represented by the formula (I), ##STR18## wherein the group ##STR19## is attached to the exo side of the norbornane ring at the 8- or 9-position, R represents an alkyl group having 1 to 6 carbon atoms, and the dotted line between carbon 3 and carbon 4 represents a saturated or ethylenically unsaturated bond.
Dependencies are inferred from the claim text.