The present invention relates to new odorous acetals which are useful as fragrance or flavor materials in particular in providing vanilla and spicy notes with a natural impression resembling vanilla absolute.

A halide compound having one or more carbon-carbon unsaturated bonds is catalytically reduced with substantially no dehalogenation to produce a reduced halide compound in which at least one of the one or more unsaturated bonds is reduced. Specifically provided is a method for producing a reduced halide compound including steps of: reacting a nickel compound, a zinc compound, and a borohydride compound in a solvent to obtain a reduction catalyst; and subjecting a halide compound having one or more carbon-carbon unsaturated bonds to catalytic reduction in the presence of the reduction catalyst to reduce at least one of the one or more carbon-carbon unsaturated bonds to thereby obtain a reduced halide compound.

A halide compound having one or more carbon-carbon unsaturated bonds is catalytically reduced with substantially no dehalogenation to produce a reduced halide compound in which at least one of the one or more unsaturated bonds is reduced. Specifically provided is a method for producing a reduced halide compound including steps of: reacting a nickel compound, a zinc compound, and a borohydride compound in a solvent to obtain a reduction catalyst; and subjecting a halide compound having one or more carbon-carbon unsaturated bonds to catalytic reduction in the presence of the reduction catalyst to reduce at least one of the one or more carbon-carbon unsaturated bonds to thereby obtain a reduced halide compound.

The present invention provides: an acetal compound represented by the following general formula (1):

##STR00001##

wherein R.sup.1 represents an alkyl group having from 1 to 12 carbon atoms, a cycloalkyl group having from 5 to 12 carbon atoms or an acyl group having from 1 to 12 carbon atoms; n represents an integer from 1 to 5; m represents an integer from 2 to 4; and Ar represents a residue obtained by removing a hydrogen atom(s) from the hydroxyl groups of a polyhydric phenol having a valence of m; and a resist composition for forming a thick resist film, including the same.

The present invention provides: an acetal compound represented by the following general formula (1):

##STR00001##

wherein R.sup.1 represents an alkyl group having from 1 to 12 carbon atoms, a cycloalkyl group having from 5 to 12 carbon atoms or an acyl group having from 1 to 12 carbon atoms; n represents an integer from 1 to 5; m represents an integer from 2 to 4; and Ar represents a residue obtained by removing a hydrogen atom(s) from the hydroxyl groups of a polyhydric phenol having a valence of m; and a resist composition for forming a thick resist film, including the same.

The present invention provides: an acetal compound represented by the following general formula (1):

##STR00001##

wherein R.sup.1 represents an alkyl group having from 1 to 12 carbon atoms, a cycloalkyl group having from 5 to 12 carbon atoms or an acyl group having from 1 to 12 carbon atoms; n represents an integer from 1 to 5; m represents an integer from 2 to 4; and Ar represents a residue obtained by removing a hydrogen atom(s) from the hydroxyl groups of a polyhydric phenol having a valence of m; and a resist composition for forming a thick resist film, including the same.

A halide compound having one or more carbon-carbon unsaturated bonds is catalytically reduced with substantially no dehalogenation to produce a reduced halide compound in which at least one of the one or more unsaturated bonds is reduced. Specifically provided is a method for producing a reduced halide compound including steps of: reacting a nickel compound, a zinc compound, and a borohydride compound in a solvent to obtain a reduction catalyst; and subjecting a halide compound having one or more carbon-carbon unsaturated bonds to catalytic reduction in the presence of the reduction catalyst to reduce at least one of the one or more carbon-carbon unsaturated bonds to thereby obtain a reduced halide compound.

A halide compound having one or more carbon-carbon unsaturated bonds is catalytically reduced with substantially no dehalogenation to produce a reduced halide compound in which at least one of the one or more unsaturated bonds is reduced. Specifically provided is a method for producing a reduced halide compound including steps of: reacting a nickel compound, a zinc compound, and a borohydride compound in a solvent to obtain a reduction catalyst; and subjecting a halide compound having one or more carbon-carbon unsaturated bonds to catalytic reduction in the presence of the reduction catalyst to reduce at least one of the one or more carbon-carbon unsaturated bonds to thereby obtain a reduced halide compound.

To provide a novel method for producing a halogenated acrylic acid derivative. A compound represented by the formula (1): ##STR00001##
(wherein each of R.sup.1 and R.sup.2 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom, or R.sup.1 and R.sup.2 together form a ring, R.sup.3 is a monovalent group capable of being desorbed by R.sup.3OH removal reaction, and each of R.sup.4 and R.sup.5 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom) and having a boiling point of at most 500 C., is subjected to R.sup.3OH removal reaction in a vapor phase in the presence of a solid catalyst to obtain an ethene derivative represented by the formula (2): ##STR00002##
the ethene derivative represented by the formula (2) and a halogenated methane represented by the formula (3):
CHXYZ(3)
(wherein each of X, Y and Z which are independent of one another, is a halogen atom) are reacted in the presence of a basic compound and a phase transfer catalyst, to obtain a cyclopropane derivative represented by the formula (4): ##STR00003##
and the cyclopropane derivative represented by the formula (4) is reacted by heating in a liquid phase or in a vapor phase to obtain a halogenated acrylic acid ester derivative represented by the formula (5): ##STR00004##

To provide a novel method for producing a halogenated acrylic acid derivative. A compound represented by the formula (1): ##STR00001##
(wherein each of R.sup.1 and R.sup.2 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom, or R.sup.1 and R.sup.2 together form a ring, R.sup.3 is a monovalent group capable of being desorbed by R.sup.3OH removal reaction, and each of R.sup.4 and R.sup.5 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom) and having a boiling point of at most 500 C., is subjected to R.sup.3OH removal reaction in a vapor phase in the presence of a solid catalyst to obtain an ethene derivative represented by the formula (2): ##STR00002##
the ethene derivative represented by the formula (2) and a halogenated methane represented by the formula (3):
CHXYZ(3)
(wherein each of X, Y and Z which are independent of one another, is a halogen atom) are reacted in the presence of a basic compound and a phase transfer catalyst, to obtain a cyclopropane derivative represented by the formula (4): ##STR00003##
and the cyclopropane derivative represented by the formula (4) is reacted by heating in a liquid phase or in a vapor phase to obtain a halogenated acrylic acid ester derivative represented by the formula (5): ##STR00004##