The present invention provides a process for preparing an unsaturated alcohol of the formula (I), wherein one of R.sup.1 and R.sup.2 is preferably C.sub.2-C.sub.10-alkyl or C.sub.2-C.sub.10-alkenyl containing one double bond and the other one is preferably hydrogen or methyl; R.sup.3 is preferably hydrogen; which comprises subjecting an educt composition including at least 75% by weight of an unsaturated aldehyde of the formula (II) wherein R.sup.1, R.sup.2 and R.sup.3 preferably have the above defined meanings, to a hydrogenation in the presence of a catalyst and a tertiary amine; wherein the tertiary amine is used in an amount ranging from 0.001 to 0.7% by weight, based on the total amount of the liquid reaction mixture. The invention further relates to the nerol compound obtainable by the inventive process, to a fragrance or aroma substance composition comprising the nerol compound obtainable by the inventive process, to a method for imparting and/or intensifying an odor or flavor of a product, and also to perfumed or aromatized products comprising a nerol compound obtainable by the inventive process. ##STR00001##

The present invention relates to a process of hydrogenating an alkyne selectively to an alkene by hydrogen using a hydrogenation catalyst which is palladium supported on a carrier in the presence of an additive mixture of an organic phosphorus compound (AP) and an organic sulphur compound (AS).

The present invention relates to a process of hydrogenating an alkyne selectively to an alkene by hydrogen using a hydrogenation catalyst which is palladium supported on a carrier in the presence of an additive mixture of an organic phosphorus compound (AP) and an organic sulphur compound (AS).

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (4), the method including the steps of: hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound (1) to obtain 7-methyl-3-methylene-7-octenal (2); reducing the 7-methyl-3-methylene-7-octenal (2) to obtain 7-methyl-3-methylene-7-octenol (3); and esterifying the 7-methyl-3-methylene-7-octenol (3) to obtain a 7-methyl-3-methylene-7-octenyl carboxylate compound (4). ##STR00001##

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (4), the method including the steps of: hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound (1) to obtain 7-methyl-3-methylene-7-octenal (2); reducing the 7-methyl-3-methylene-7-octenal (2) to obtain 7-methyl-3-methylene-7-octenol (3); and esterifying the 7-methyl-3-methylene-7-octenol (3) to obtain a 7-methyl-3-methylene-7-octenyl carboxylate compound (4). ##STR00001##

Provided are a fluorine-containing ether compound, fluorine-containing ether composition and coating liquid that can form a surface layer having excellent durability, an article having a surface layer that has excellent durability, and a compound that is useful as a raw material of a fluorine-containing ether compound. The fluorine-containing ether compound is represented by the following formula (A1) or formula (A2):

R.sup.f—O—(R.sup.f1O).sub.m—R.sup.f2[—R.sup.1—C(—R.sup.2-T).sub.a(—R.sup.3).sub.3-a].sub.b  Formula (A1)

[(T-R.sup.2—).sub.a(R.sup.3—).sub.3-aC—R.sup.1—].sub.bR.sup.f2—O—(R.sup.f1O).sub.m—R.sup.f2[—R.sup.1—C(—R.sup.2-T).sub.a(-R.sup.3).sub.3-a].sub.b   Formula (A2) wherein each of the reference signs in the formulas are as described in the specification.

Provided are a fluorine-containing ether compound, fluorine-containing ether composition and coating liquid that can form a surface layer having excellent durability, an article having a surface layer that has excellent durability, and a compound that is useful as a raw material of a fluorine-containing ether compound. The fluorine-containing ether compound is represented by the following formula (A1) or formula (A2):

R.sup.f—O—(R.sup.f1O).sub.m—R.sup.f2[—R.sup.1—C(—R.sup.2-T).sub.a(—R.sup.3).sub.3-a].sub.b  Formula (A1)

[(T-R.sup.2—).sub.a(R.sup.3—).sub.3-aC—R.sup.1—].sub.bR.sup.f2—O—(R.sup.f1O).sub.m—R.sup.f2[—R.sup.1—C(—R.sup.2-T).sub.a(-R.sup.3).sub.3-a].sub.b   Formula (A2) wherein each of the reference signs in the formulas are as described in the specification.

The present invention provide for preparing a formylalkenyl alkoxymethyl ether compound of the following general formula (2): R.sup.3CH.sub.2OCH.sub.2O(CH.sub.2).sub.aCH═CHCHO (2), wherein R.sup.3 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and “a” represents an integer of 1 to 10, the process comprising: hydrolyzing a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R.sup.3CH.sub.2OCH.sub.2O(CH.sub.2).sub.aCH═CHCH(OR.sup.1)(OR.sup.2) (1), wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.1 and R.sup.2 may form together a divalent hydrocarbon group, R.sup.1-R.sup.2, having 2 to 10 carbon atoms; and R.sup.3 and “a” are as defined above, in the presence of an acid while removing an alcohol compound thus generated to form the formylalkenyl alkoxymethyl ether compound (2).

The present invention relates to a haloalkenyl alkoxymethyl ether compound of the following general formula (1): R.sup.1CH.sub.2OCH.sub.2OCH.sub.2CH.sub.2CH═CH(CH.sub.2).sub.aX.sup.1 (1) wherein R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X.sup.1 represents a halogen atom, and “a” represents an integer of 3 to 14. The present invention also relates to processes for preparing a terminal conjugated alkadien-1-yl acetate compound of the following general formula (5): CH.sub.2═CHCH═CH(CH.sub.2).sub.aOAc (5) wherein “a” is as defined above, and Ac represents an acetyl group, and a terminal conjugated alkadien-1-ol compound of the following general formula (6): CH.sub.2═CHCH═CH(CH.sub.2).sub.aOH (6) wherein “a” is as defined above, from the haloalkenyl alkoxymethyl ether compound (1).

The present invention relates to a haloalkenyl alkoxymethyl ether compound of the following general formula (1): R.sup.1CH.sub.2OCH.sub.2OCH.sub.2CH.sub.2CH═CH(CH.sub.2).sub.aX.sup.1 (1) wherein R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X.sup.1 represents a halogen atom, and “a” represents an integer of 3 to 14. The present invention also relates to processes for preparing a terminal conjugated alkadien-1-yl acetate compound of the following general formula (5): CH.sub.2═CHCH═CH(CH.sub.2).sub.aOAc (5) wherein “a” is as defined above, and Ac represents an acetyl group, and a terminal conjugated alkadien-1-ol compound of the following general formula (6): CH.sub.2═CHCH═CH(CH.sub.2).sub.aOH (6) wherein “a” is as defined above, from the haloalkenyl alkoxymethyl ether compound (1).