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##

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##

A method includes a step of reacting a hydrocarbon-containing gas with an oxygen-containing gas to form a first product blend in a reactor. The first product blend includes a blend of partially oxygenated compounds. The blend of partially oxygenated compounds is provided to one or more reactive distillation stations; and The blend of partially oxygenated compounds is converted to a second product blend at one or more reactive distillation stations. Characteristically, the second product blend includes a mixture comprising a at least two of components selected from acetals, ethers, alcohols, esters, and alkenes.

A method includes a step of reacting a hydrocarbon-containing gas with an oxygen-containing gas to form a first product blend in a reactor. The first product blend includes a blend of partially oxygenated compounds. The blend of partially oxygenated compounds is provided to one or more reactive distillation stations; and The blend of partially oxygenated compounds is converted to a second product blend at one or more reactive distillation stations. Characteristically, the second product blend includes a mixture comprising a at least two of components selected from acetals, ethers, alcohols, esters, and alkenes.

A method of making spirogalbanone includes the steps of: (a) subjecting ethynylspirodecanol to a Rupe rearrangement to give a compound of the formula I ##STR00001## (b) converting the compound of (a) to a C1-C4 alkyl acetal; (c) subjecting the acetal to a trans-acetalization reaction with allyl alcohol in the presence of a mild acid catalyst; (d) heating the product of (c) in the presence of an acid catalyst to give an allylenolether; and (e) subjecting the product of (d) to a Claisen rearrangement to give spirogalbanone. The method affords an easier and more efficient method of preparation.

A method of making spirogalbanone includes the steps of: (a) subjecting ethynylspirodecanol to a Rupe rearrangement to give a compound of the formula I ##STR00001## (b) converting the compound of (a) to a C1-C4 alkyl acetal; (c) subjecting the acetal to a trans-acetalization reaction with allyl alcohol in the presence of a mild acid catalyst; (d) heating the product of (c) in the presence of an acid catalyst to give an allylenolether; and (e) subjecting the product of (d) to a Claisen rearrangement to give spirogalbanone. The method affords an easier and more efficient method of preparation.

A method of making spirogalbanone includes the steps of: (a) subjecting ethynylspirodecanol to a Rupe rearrangement to give a compound of the formula I

##STR00001## (b) converting the compound of (a) to a C1-C4 alkyl acetal; (c) subjecting the acetal to a trans-acetalisation reaction with allyl alcohol in the presence of a mild acid catalyst; (d) heating the product of (c) in the presence of an acid catalyst to give an allylenolether; and (e) subjecting the product of (d) to a Claisen rearrangement to give spirogalbanone.

The method affords an easier and more efficient method of preparation.

A method of making spirogalbanone includes the steps of: (a) subjecting ethynylspirodecanol to a Rupe rearrangement to give a compound of the formula I

##STR00001## (b) converting the compound of (a) to a C1-C4 alkyl acetal; (c) subjecting the acetal to a trans-acetalisation reaction with allyl alcohol in the presence of a mild acid catalyst; (d) heating the product of (c) in the presence of an acid catalyst to give an allylenolether; and (e) subjecting the product of (d) to a Claisen rearrangement to give spirogalbanone.

The method affords an easier and more efficient method of preparation.

Disclosed is an industrial method for efficient production of an ,-difluoroaldehyde compound, which includes reaction of an ,-difluoroacetate with hydrogen gas (H.sub.2) in the presence of a ruthenium catalyst and a base. By the adoption of specific reaction conditions (catalyst, base, pressure etc.), it is possible to produce the target ,-difluoroaldehyde compound with a high conversion rate and high selectivity.