TW201036943A - Method for producing benzaldehyde compound - Google Patents

Abstract

The invention provides a benzaldehyde acetal compound that is represented by the formula (3): (in the formula, Q represents a hydrogen atom or a halogen atom. Ar represents a phenyl group optionally substituted by at least one selected from the group consisting of an alkyl group having 1 to 4 carbon numbers and a halogen atom. R represents an alkyl group having 1 to 4 carbon numbers.)

Description

201036943 VI. Description of the Invention: [Technical Field to Which the Invention Is Ascribed] The present invention relates to a method for producing a benzofuraldehyde compound. [Prior Art] A benzoquinone compound represented by the following formula (4) is useful as an intermediate for producing a bactericide (for example, refer to Japanese Patent Laid-Open Publication No. Hei 9-95462 and U.S. Patent No. 5,145,980):

(wherein Q represents a hydrogen atom or a halogen atom, and Ar represents a phenyl group which may be substituted with at least one selected from the group consisting of an alkyl group having 1 to 4 carbon atoms and a halogen atom). As a method for producing a benzaldehyde compound represented by the formula (4), a method for oxidizing a corresponding halogenated indole compound is disclosed in Japanese Laid-Open Patent Publication No. Hei 9-95462, No. 5245980 In the publication, a method of oxidizing a corresponding benzonitrile compound is disclosed. SUMMARY OF THE INVENTION The present invention provides: <1> A benzaldehyde acetal compound represented by the formula (3):

139604.doc 201036943 (wherein Q represents a hydrogen atom or a halogen atom, and Ar represents a phenyl group R which may be substituted with at least one selected from the group consisting of an alkyl group having a carbon number of 1 to 4 and a halogen atom; <2> The benzoquinal acetal compound of <1> wherein r is a methyl group; <3> such as a benzoquinone acetal compound, wherein Ar is a a phenyl group substituted with at least one alkyl group having a carbon number of 1 to 4; <4> a benzaldehyde acetal compound according to <3> wherein the phenyl group substituted with at least one alkyl group having 1 to 4 carbon atoms is <5> The benzoquinal acetal compound of <1> wherein r is a fluorenyl group and 2,5, dimethylphenyl 'q is a hydrogen atom; <6> A method for producing a benzaldehyde compound, which is a method for producing a benzaldehyde compound represented by the formula (4):

(wherein Q and Ar respectively have the same meanings as described above); characterized in that the benzalic acid compound represented by the formula (3) is reacted with water in the presence of an acid:

Ar represents a group which may be substituted by at least one selected from carbon (wherein Q represents a hydrogen atom or a dentate atom, an alkyl group having an A number of 1 to 4, and a halogen atom; 139604.doc 201036943 phenyl' R represents an alkyl group having a carbon number of 1 to 4; <7> The method for producing a benzofural compound according to <6>, wherein the acid is a Bronsted acid; <8> a benzene such as <7> A method for producing a furfural compound, wherein the Brucene acid is sulfuric acid; <9> A method for producing a phenylfurfural dialkyl acetal compound, which is produced by the benzaldehyde dialkyl condensation represented by the formula (3) Aldehyde compounds:

OR

(wherein Q, Ar and R respectively have the same meanings as described above); characterized in that the benzylidene compound represented by the formula (1) is oxidized with the alkali metal alkane represented by the formula (2) Reaction:

X

(wherein Q represents a hydrogen atom or a halogen atom, and X represents a halogen atom, and the phenyl group which may not be substituted with at least one selected from the group consisting of an alkyl group having a carbon number of 丨4 and a halogen atom); y., R represents an alkyl group having a carbon number of 1 to 4, and Μ represents an alkali metal atom; and <1〇> a method for producing a benzofural dialkyl acetal compound according to <9>, 139604 .doc 201036943 In the presence of a moth or a moth compound, the agglomerate represented by the formula (1) is reacted with the metal oxide represented by the formula (7); <11> such as <1G> The method for producing a f-dialkyl-based acid-compounding compound, wherein the iodine compound is an alkali metal iodide; and the benzoic acid-based condensed compound of any one of <9> to <11;> (4) A subunit-based di-compound represented by ^(1) and an alkali-metal sinter oxide represented by formula (7) in the presence of a target transfer catalyst, a benzoyl dialkyl acetal compound represented by formula (7) The method for producing a phase transfer catalyst is a quaternary salt; <14> a benzylidene dihalide, which is represented by the formula (丨):

(wherein Q represents a hydrogen atom or a _ atom, χ represents a functional atom, & represents a stupid group which may be substituted with at least one selected from the group consisting of an alkyl group having a carbon number of 4 and a spectrin atom; <15> A sub-block dihalide of <14> wherein the acne atom is a chlorine atom; <16> such as "cedar or". a subunit dentate, wherein Ar is a phenyl group substituted with at least one alkyl group having 1 to 4 carbon atoms; <17><16>, a benzylidene dihalide of <16>, wherein at least one carbon The phenyl group substituted with an alkyl group of 1 to 4 is 2,5-dimethylphenyl; , Ar <18> such as the benzylidene dihalide of <14> wherein X is a gas atom 139604.doc -6- 201036943 is 2,5-dimercaptophenyl, Q is a hydrogen atom; <19> A method for producing a box of lysine-upper-salt, which is produced by the formula (1) Sub-base two-chemicals:

X

a group (wherein Q, X and Ar respectively have the same meanings as defined above); characterized in that the benzidine monohalide represented by the formula (5) is represented by the formula (6) in the presence of a base Phenol compound reaction:

(5) (wherein Q and X respectively represent the same meanings as described above); (wherein, Ar represents the same meaning as described above); <20>, such as <19> of benzylidene dihalide A method in which a mixture of a phenol compound and a base represented by hydrazine () is added to a benzylidene dihalide represented by the formula (5); for example, <19> or <20> A method for producing a benzylidene bis-compound, wherein a sub-density bidentate represented by the formula (5) is reacted with a benzoquinone compound represented by the formula (6) in the presence of a phase transfer catalyst 2> A method for producing a stupid formaldehyde compound, which comprises the following steps: 139604.doc 201036943 The following steps are carried out: (4) reacting a sub-denier bidentate represented by the formula (1) with a gold-like oxide as shown, to obtain a formula ( The manuscript indicates an alkyl acetal compound: + T岐一

(1) (wherein 'Q represents a hydrogen atom', a prime atom, χ represents a _ prime atom, and & represents a substitution by at least one selected from the group consisting of an alkyl group having a carbon number of 1 to 4 and a functional atom. (笨)); ROΜ (2) (wherein, R is not a carbon number for the burning of the base 4, the test of the metal atom);

(wherein, Q, Ar and R respectively represent the same meanings as described above) and (B) reacting the phenylfurfural acetal compound represented by the formula (3) with water in the presence of an acid, which is known by the formula (4) The abbreviated aldehyde compound represented:

(wherein, Q and Ar respectively represent the same meanings as described above); 139604.doc 201036943 <23> The method for producing a benzaldehyde compound according to <22> further comprising (c) in the presence of a base The step of reacting a benzalyl halide represented by the formula (5) with a benzene compound represented by the formula (6) to obtain a sub-denomeric bis-form represented by the formula (1):

X

Ο (wherein Q and X respectively represent the same meaning as above);

Ar-ΟΗ (6) (wherein 'Ar means the same meaning as above);

(wherein, Q, X and Ar respectively represent the same meanings as described above). [Embodiment] First, a benzaldehyde acetal compound represented by the formula (3) (hereinafter, simply referred to as an acetal compound (3)) will be described:

OR

In the gas, Q represents a hydrogen atom or a halogen atom, and Ar represents 139604.doc 201036943 phenyl which may be substituted by at least one selected from the group consisting of a group of a carbon group and a group of a carbon atom, and R represents a carbon number of 1. ~4 of the base). In the formula of the compound (7), Q represents a hydrogen atom or a hydrogen atom. As Λ忐i π 7 is bounded by a better atom, a moth atom can be enumerated as a gas atom, a chlorine atom, or a compound (3), and ^ can be selected from a carbon number of a phenyl group substituted with at least one of the groups of atoms. Examples of the hospital base having a carbon number of 1 to 4 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a t-butyl group. Examples of the dentinogen + include an I atom and chlorine. Atoms, etc. The phenyl group which may be substituted with at least one selected from the group consisting of a carbon number of (4) and a γ atom may be exemplified by an I group, a 2-mercaptophenyl group, a 4-methylphenyl group, and a 5-phenyl group. Methyl phenyl, 2,5-dimethylphenyl, 2 4 dimethylphenyl, 2.6-dimethylphenyl, 2,4,6-trimethylphenyl, 2-ethylphenyl , 4-ethylphenyl, 5-ethylphenyl, 2,5·diethylphenyl, 2,4-diethylphenyl, 2.6-diethylphenyl, 2,4,6_three Ethylphenyl, 2-propylphenyl, 'propylphenyl, 5-propylphenyl, 2,5-dipropylphenyl, 2,4-dipropylphenyl, 2.6-dipropyl Phenyl, 2,4,6-tripropylphenyl, 2-isopropylphenyl, 4-isopropylphenyl, 5-isopropylphenyl, 2,5-isopropylphenyl, 2 ,4-diisopropylphenyl' 2,6-diisopropylphenyl, 2,4,6-triisopropylphenyl, 2-butylphenyl, 4-butylphenyl, 5-butyl Phenylphenyl, 2,5-dibutylphenyl, 2,4-dibutylphenyl, 2,6-dibutylphenyl' 2,4,6-tributylphenyl, 2-isobutyl Phenylphenyl, 4-isobutylphenyl, 5-isobutylphenyl, 2,5-diisobutylphenyl, 2,4-diisobutylphenyl, 2,6-diisobutyl Phenyl, 2,4,6-three Butylphenyl, 2-tert-butylphenyl, 4-tert-butylphenyl, 5-t-butylbenzene 139604.doc -10· 201036943 base, 2,5-di-t-butylbenzene Base, 2,4-di-t-butylphenyl, 2,6-di-tert-butylphenyl, 2,4,6-tri-tert-butylphenyl, 2-fluorophenyl, 4 Fluorophenyl, 2,4-difluorophenyl, 2,4,6-trifluorophenyl, pentafluorophenyl, 2-p-phenyl, 4-phenylphenyl, 2,4-dichlorophenyl, 2,4,6-trichlorophenyl, pentachlorophenyl, and the like. Among them, preferred is a phenyl group substituted by at least one alkyl group having a carbon number, and more preferably a 2,5-dimethylphenyl group. The condensed compound (3) is a novel compound, and specific examples thereof include 2-(phenoxymercapto)benzoquinone dimethyl acetal and 2-gas 2-methylphenoxy fluorenyl benzene. Formaldehyde dimethyl acetal, 2-(2-ethylphenoxymethyl)benzaldehyde dimethyl acetal, 2-(2-isopropylphenoxymethyl) benzofural dimethyl acetal , 2-(4-methylphenoxymethyl)benzaldehyde dimethyl acetal, 2—(4·isopropyl phenyloxymethyl)benzaldehyde dimethyl acetal, 2-(2,5- Dimethylphenoxymethyl) benzaldehyde dimethyl acetal, 2-(2,5-diethylphenoxymethyl)benzaldehyde dimethyl acetal, 2-(2,5-diiso) Propylphenoxymethyl)benzaldehyde dimethyl acetal, 2-(2,4,5-trimethylphenoxymethyl)benzaldehyde dimethyl acetal, 2_ (2,4,6- Dimethylphenoxy) benzoyl via dimethyl condensation, 2_(3,4,5-trimethylphenoxymethyl)benzaldehyde dimethyl acetal, 2_(2,4,5_ Trimethylphenyloxymethyl)benzaldehyde dimethyl acetal, 2-(2,5-dimethylphenoxymethyl)_3_chlorobenzaldehyde dimethyl acetal, 2_(2,5_2 Methylphenoxymethyl)_4_chlorobenzaldehyde dimethyl acetal, 2- (2,5-Dimethylphenoxymethyl)_5-chlorobenzaldehyde dimethyl acetal, 2-(2,5-dimethylphenyloxymethyl)_6_gasaldehyde dimethyl condensate Aldehyde, 2-(2,5-diethylphenoxymethyl)_3_chlorobenzaldehyde dimethyl condensate, 2-(2,5-diethylphenoxymethyl)-4 chlorobenzoquinone Aldehyde dimethyl acetal, 2-(2,5-diethylphenoxymethyl)_5. chlorobenzaldehyde dimethyl acetal, 2_139604.doc 201036943 (2,5-ethylphenoxymethyl) Benzene-6-gas benzoic acid: dimethyl condensate, 2_(2,5. monoisopropylphenoxymethyl)-3-chlorobenzoic acid dimethyl condensate, 2_(2,5_two Isopropyl basic oxyf-yl)-4-chlorobenzene f via dimethyl condensate, 2_(2,5-diisopropylphenoxymethyl)-5-chlorobenzaldehyde decyl acetal, 2_ (2,5·diisopropylphenyloxymethyl)-6-gasbenzyl dimethyl thiophene, 2_(2,5-dimethylphenoxymethyl)-4-bromophenylfurfural Dimethyl acetal, 2_(2,5-diethylphenoxymethyl)-4-bromobenzaldehyde dimethyl acetal, 2_(2,5-diisopropylphenoxymethyl)- 4-bromobenzaldehyde dimethyl acetal, 2_(2,5-dimethylphenoxymethyl)_4_iodobenzaldehyde dimethyl acetal, 2-(2,5-di Nonylphenoxymethyl)benzaldehyde diethyl acetal, 2-(2,5-dimercaptophenoxymethyl)phenylfurfural dipropyl acetal, 2-(2,5-dimethyl Phenyloxyindenyl)benzaldehyde dibutyl acetal, 2_(2,5-monomethylphenoxymethyl)phenylfurfural diisopropyl acetal, 2_(2,5-dimercaptophenoxy Methyl)benzaldehyde diisobutyl acetal, 2_(2,5-dimercaptophenoxyfluorenyl) benzoquinone di-t-butyl condensed or the like. By reacting the acetal compound (3) with water in the presence of an acid, a paraformaldehyde compound represented by the formula (4) (hereinafter, simply referred to as a benzaldehyde compound (4)) can be obtained:

(wherein Q and Ar respectively have the same meanings as described above). The acid may, for example, be a Brilliant acid such as hydrochloric acid, sulfuric acid or nitric acid, and more preferably sulfuric acid. The acid is usually used by a commercial person. If necessary, it can be diluted with water or after the 139604.doc 201036943/grain. The acid is usually used in the form of an aqueous solution. The amount of the acid used is usually 〇1 mol or more, preferably 1 to 5 mol, based on 1 mol of the acetal compound (3). The amount of water used is usually 2 moles per gram of the acetal compound (3), and there is no upper limit for the amount of water used, and water can be used as a solvent to use a large excess of water. 3) The reaction with water is usually carried out in the presence of an organic solvent. Examples of the organic solvent include aromatic private hydrocarbons such as xylene, toluene and benzene; pentane, hexane, heptane, cyclohexane, etc. An aliphatic hydrocarbon solvent; an ether solvent such as diethyl ether, a third butyl methyl ether or a cyclopentyl oxime ether; an alcohol solvent such as methanol, ethanol, butanol, isopropanol, isobutanol or tert-butanol; Preferably, it is an aromatic hydrocarbon solvent, more preferably xylene and toluene. The amount of organic solvent used is not limited, and from the viewpoint of volume efficiency, usually relative to 1 part by weight of the acetal compound (3) The reaction degree is usually 丨c or more and the boiling point of the solvent or less, preferably 10 to 100 〇c. The reaction can be carried out under normal pressure or under pressure. Gas chromatography, high performance liquid chromatography, magnetic resonance The usual analysis method is used to confirm the progress of the reaction. The reaction can be carried out by mixing the acid, the shrinkage compound (3) and water, and the sigma sequence of «Xuan et al. is infinitely ^, preferably adjusted to the reaction. An aqueous solution of an acid is added to the acid compound (3) at a temperature. Thus, a reaction mixture containing the benzoic acid compound (4) can be obtained, and the reaction mixture can be obtained, for example, directly or after washing, by 139604.doc •13-201036943, to obtain benzene. The furfural compound (4) can be further purified by a usual purification method such as recrystallization, distillation or column chromatography, as the obtained benzaldehyde compound (4). Examples of the compound (4) include 2-(phenoxyindenyl)benzaldehyde, 2-(2-methylphenoxymethyl)benzaldehyde, and 2-(2-ethylphenoxyfluorenyl)benzaldehyde. 2-(2-isopropylphenoxyindolyl)benzaldehyde, 2-(4-methylphenoxyindolyl)benzaldehyde, 2-(4-isopropylphenoxymethyl)benzaldehyde, 2 -(2,5-dimethylphenoxymethyl)benzaldehyde, 2_(2,5-diethylphenoxymethyl)benzaldehyde, 2-(2,5- Isopropylphenoxymethyl)benzaldehyde, 2-(2,4,5-trimethylphenoxymethyl)benzofural, 2_(2,4,6-trimethylphenoxyfluorenyl) Benzaldehyde, 2-(3,4,5-trimethylphenoxymethyl)benzoic acid, 2-(2,4,5-dimethylphenoxymethyl)benzoic acid, 2_(2) ,5-dimercaptophenoxymethyl)-3-gasbenzaldehyde, 2-(2,5-dimethylphenoxymethyl)_4_qibene, 2-(2,5-a Methylphenoxymethyl)_5_gas benzoic acid, 2_(2,5-dimethylphenoxymethyl)_6-chlorobenzaldehyde, 2-(2,5-diethylphenoxymethyl )_ 3-chlorobenzaldehyde, 2·(2,5-diethylphenoxymethyl)·4_chlorobenzaldehyde, 2_(2,5-diethylphenoxymethyl)_5_gasbenzene Furfural, 2_(2,5-diethylphenoxymethyl)-6-chlorobenzaldehyde, 2-(2,5-diisopropylphenoxymethyl)_3_chlorobenzaldehyde, 2- (2,5-diisopropylphenoxymethyl)_4_chlorobenzaldehyde, 2_(2,5-isopropylphenoxymethyl)-5-gasbenzaldehyde, 2-(2,5- Diisopropylphenoxymethyl)-6-chlorobenzamide, 2-(2,5-dimethylphenoxymethyl)_4-bromobenzaldehyde, 2-(2,5-diethylbenzene Oxymethyl)_4_bromobenzaldehyde, 2_(2,5_two Propyl-phenoxymethyl) 4 "smelly ㉟ benzyloxy, 2- (2,5-dimethylphenoxy-methyl) _ I39604.doc -14- 201036943 4- iodobenzene Yue aldehyde. The acetal compound (3) can be obtained by using a benzylidene compound represented by the formula (1) (hereinafter, abbreviated as a benzylidene dihalide ruthenium) and a formula (2). The alkali metal alkoxide (hereinafter, abbreviated as alkali metal alkoxide (2)) is represented by: 疋

(wherein, Q and Ar respectively have the same meanings as described above, 乂 represents a halogen atom); ’'RO—Μ (2) (wherein R represents the same meaning as above, and 1^ represents an alkali metal atom). In the formula of the benzylidene di-A compound (1), X represents a functional atom, and the _ 素 atom may be a gas atom, a bromine atom or an iodine atom, preferably a chlorine atom.

The benzal dihalide (1) is also a novel compound, and specific examples thereof include 2-(phenoxymethyl)throate, 2-(2-methylphenoxymethyl)hexanthene, 2_ ( 2-ethylphenoxymethyl)thranium, 2_(2-isopropylphenoxymethyl as chlorine, 2-(4-methylphenoxymethyl)throate, 2_(4_isopropyl Phenyloxymethyl)cetidine, 2-(2,5·dimethylphenoxymethyl)hexadecane, 2-(2 5 -diethylphenoxymethyl)hexadecane, 2-(2 ,5-diisopropylphenoxymethyl)cetidine, 2_(2,4,5-trimethylphenoxymethyl)benzyl chloride, 2_(2,4,6-tridecylphenoxymethyl) Benzyl chloride, 2-(3,4,5-trimethylphenoxymethyl)throate, 2_(2,4,5-trimethylphenoxymethyl)benzyl chloride, 2-(2 ,5-dimethylphenoxymethyl)_3_chlorobenzyl chloride, 2_139604.doc 15 201036943 (2,5-dimercaptophenoxymethyl)-4-abenzyl chloride, 2-(2, 5-dimercaptophenoxymethyl)-5-gasbenzyl, 2-(2,5-dimercaptophenoxymethyl)-6-gasbenzyl chloride, 2-(2,5-diethylbenzene Oxymethyl) _3·gas benzyl, 2-(2,5-diethylphenoxymethyl)-4-benzylidene, 2-(2,5-ethylphenoxyfluorenyl) _5_ benzyl chloride, 2_ (2,5-diethyl Phenoxymethyl)_6-chlorobenzyl chloride, 2_(2,5-diisopropylphenoxyindolyl)-3-chlorobenzyl chloride, 2-(2,5-diisopropylphenoxyhydrazine Base)_4_chlorobenzyl chloride, 2-(2,5-diisopropylphenoxymethyl)-5-chlorobenzyl chloride, 2-(2,5-diisopropylphenoxymethyl)-6- Gas-based gas, 2·(2,5-diethylphenoxyfluorenyl) node/odor, 2-(2,5-diethylphenoxyfluorenyl)benzyl iodide, 2(2,5_two Nonylphenoxymethyl)-4-bromobenzyl bromide, 2-(2,5-diethylphenoxymethyl)-4-bromobenzyl bromide, 2_(2,5-diisopropylphenoxy Methyl)·4·bromobenzyl bromide, 2-(2,5-dimercaptophenoxymethyl)-4-benzylidene, etc. In the formula of the metal-fired oxide (2), M represents the metal test An atom, as a metal atom, can be exemplified as a raccoon atom, a nano atom, an unloading atom, an atomic atom, an apo atom, or a recorded atom. It is preferably a sodium atom. As a metal oxide (7), a oxidized clock, B Lithium oxide, such as lithium oxide, propenium oxide, lithium butoxide oxide, isobutyl oxide clock, isobutyl oxidation clock, lithium dibutyl oxide, etc.; sodium methoxide, sodium ethoxide, propane oxidation, sodium butoxide, isopropyl Sodium oxide, different Sodium oxide, sodium sulphate, sodium sulphate; oxidative dehydration of 'ethoxy ethoxylate, propane oxidative unloading, butyl oxidized ^ potassium isopropoxide, isobutyl oxidative unloading, third potassium oxychloride, etc. Ethmium oxyhydroxide, arsenic trioxide, strontium oxychloride, propylene oxide: strontium; oxidized oxides such as cerium oxide; third butyl oxide; oxidized oxidized planer, arsenic trioxide, butyl oxidized, bismuth bismuth oxide , Isobutyl 139604.doc •16· 201036943 Aldehyde oxide planer of antimony oxide, third antimony oxide, etc.; and antimony ruthenium oxide, antimony ethoxide, antimony propoxide, antimony trioxide, antimony isopropoxide, isobutyl oxide chain An alkoxylated ruthenium or the like such as a third ruthenium oxide. Of these, sodium alkoxide is preferred, and sodium bismuth oxide is more preferred. The metal oxide oxide (2) can be used commercially, and can also be prepared by reacting the corresponding alcohol with a metal hydride or a metal hydroxide. Further, the preparation of the alkali metal alkoxide (2) and the benzal bromide can be simultaneously carried out by mixing a benzal dihalide (rhodium), a corresponding alcohol with an alkali metal hydroquinone or an alkali metal hydroxide. Reaction of a bishalide halide (1) with an alkali metal alkoxide. The amount of the alkali metal alkoxide (2) used is not limited, and is usually from 2 to 10 moles, preferably from 3 to 5, relative to the benzal halide (1). Moor. The reaction of the benzal halide (1) with the alkali metal alkoxide (2) can be carried out in the presence of a solvent or in the absence of a solvent. It is preferred that Q be carried out in the presence of a solvent. The solvent may, for example, be xylene, f benzene or aryl (4) smouldering: aliquot: an aliphatic hydrocarbon solvent such as pentane, hexane, heptane or cyclohexane; tetrahydrofuran. (4) agents such as methanol, ethanol, butanol, isopropanol, isobutanol, and tert-butanol, etc.; Among them, an alcohol solvent is preferred, and an alcohol solvent having the same alkoxy group as the alkoxy group of the metal oxide oxide (2) used is more preferred. The amount of the solvent to be used is not limited, and from the viewpoint of economy, it is usually used in an amount of (10) by weight of 139604.doc 201036943 or less based on 1 part by weight of the sub-density bidentate (1). By the reaction of the sub-density compound (1) and the metal-burning oxide (2) in the presence of a phase transfer catalyst, the reaction can be carried out more smoothly. = Phase transfer catalyst, for example: a quaternary ammonium salt of a quaternary ammonium salt such as butyl ammonium bromide, benzyl triethyl ammonium hydride, tetra-n-butyl ammonium hydrogen sulfate or trioctyl methyl ammonium chloride; A compound such as 18-crown-6 or polyethylene glycol, etc., among which a quaternary ammonium salt is preferred, and a tetra-n-butyl evolution is preferred. The phase transfer catalyst is usually used in the market. The amount of the phase transfer catalyst used is usually 0.01 mol or more, preferably 0.054 mol, relative to the benzylic benzyl diamide (1)'. In addition, due to iodine or iodine The reaction of the benzalyl halide (1) with the alkali metal alkoxide (7) in the presence of the compound can also carry out the reaction more smoothly. Examples of the iodine compound include alkali metals such as potassium iodide, sodium iodide and lithium iodide. Iodide or the like is preferably an alkali metal iodide, more preferably an iodine clock. Iodine and iodine compounds are usually For the use of iodine or iodine compound, the amount of benzylidene dentate (1) is usually 〇〇1 mole or more, preferably 0.05~. 1 mole. The reaction temperature is usually -5X: above the boiling point of the solvent, preferably 10~100 ° C. The reaction can be carried out by the benzylidene di ii compound (1) and the alkali metal alkoxide 139604. Doc •18- 201036943 There is no limitation on the mixing order of the mixed yoke and yoke. It is preferred to add the test metal oxide (7) to the sub-density dentate (1) adjusted to the reaction/dish degree. It can be carried out under pressure or under pressure. The progress of the reaction can be confirmed by a usual analytical method such as gas chromatography, high performance liquid chromatography or nmr. The reaction mixture of the acid-reducing compound (3) can be obtained by reacting the Q reaction, directly or by washing with water, and then concentrating the compound (3). For the obtained acetal compound (7), recrystallization can be utilized. Further purification is carried out by a usual purification method such as a base column or a column chromatography method. The compound is directly used in the reaction with water in the presence of the above acid, and the reaction mixture may be washed with water to remove the metal oxide oxide or the like remaining in the reaction mixture, and then used in the presence of an acid with X. When the reaction mixture is used for water and the reaction mixture is washed, if necessary, an aromatic hydrocarbon solvent such as xylene, toluene or stupid, or an aliphatic hydrocarbon solvent such as pentane, hexamethylene, heptane or cyclohexane may be added. An organic solvent insoluble in water. The benzal dihalide (1) can be produced by the following method: in the presence of a base, the subunit base 2 represented by the formula (5) The dentate (hereinafter, abbreviated as sub-base diide (5)) is reacted with a compound (hereinafter, abbreviated as phenol compound (6)) represented by the formula (6): (5) 139604.doc -19. 201036943 (where Q and X respectively represent the same meaning as above)

Ar~〇H (6) (wherein Ar represents the same meaning as described above). Examples of the sub-segment-one-dentate compound (5) include 2_(gas methyl) node gas, 2_(mothyxine) knot/odor, 2_(moth methyl) knot, 3, gas·2_(chloromethyl) ) chloroplatin, heart chlorine _ 2_ (gas sulfhydryl), qi (4- ( 曱 ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( Chlorine, 5_ desert _ (bromomethyl) bromine, 5_filled _2_ (for methyl) knots, 6_gas_2_(chloromethyl) chlorobenzene, etc., in terms of availability, Preferably, it is 2-(aeromethyl)benzyl chloride. The benzylidene dentate (5) can be used commercially, or it can be used in the presence of a radical initiator or under irradiation of light. A method in which a benzene compound is reacted with a halogen (refer to Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. , 2-isopropylphenol, 4-nonylphenol, 4-isopropylphenol, 2,5-dimethylphenol, 2,5-diethylphenol, 2,5-diisopropylphenol, 2 , 4,5-trimethylphenol, 2,4,6-tridecylphenol, 3,4,5-tridecylphenol, 2-aphenol, 4-aphenol, 2-fluorophenol, 4-fluorophenol, 2,4-difluorophenol, 2,4,6-trifluorophenol, etc., preferably 2,5-dinonylphenol. The compound (6) is commercially available, and Can be used by j. Am.

Produced by a known method described in "Tetrahedron Letters", No. 30, 5215 (1989), and Japanese Patent Laid-Open No. Hei. 139604.doc -20- 201036943 An excess amount of the phenol compound (6) can be used with respect to the benzal halide (5). An excess amount of the benzylidene dihalide can also be used with respect to the phenol compound (6). ). It is preferred to use 0.1 to 10 moles of the phenol compound (6), more preferably 1 to 3 moles of the phenol compound (6), relative to the benzal halide (5). The base may, for example, be a secondary amine such as trimethylamine, triethylamine or diisopropylethylamine; or an alkali metal such as sodium methoxide, sodium ethoxide or potassium pentoxide.

An alkali metal hydroxide such as an alkoxide, lithium hydroxide, sodium hydride or potassium hydroxide; an alkali metal ruthenium such as sodium hydride, potassium hydride or lithium hydride; an alkali metal such as sodium carbonate, potassium carbonate or lithium carbonate; a carbonate; an alkali metal hydrogencarbonate such as sodium hydrogencarbonate, potassium hydrogencarbonate or lithium hydrogencarbonate. Among them, it is preferred to use a metal hydroxide, and more preferably a hydrogen hydroxide. This test is usually used directly by a commercially available person. Further, it may be diluted with water or a solvent described later and used. For the use of the base 1, it is used in a smaller amount than the benzylidene compound (5) and the phenol compound (6)! Mohr, which is usually used in an amount of more than 丨mol, which has no upper limit, is preferably 1 to 3 moles. The reaction of the sub-nodal dihalide (5) with the stupid compound (6) is usually carried out in the presence of a solvent. Examples of the solvent include aromatic smoke solvents such as xylene, toluene, and benzene; aliphatic smoke solvents such as pentyl alcohol, hexyl alcohol, and hexanone; tetrahydrofuran, = B, and butyl ketone; (4) agent such as pentyl methyl bond; nitrile solvent such as acetonitrile or propionitrile; hydrazine solvent such as methyl tertiary butyl group; amine solvent such as dimethylformamide; dimethyl benzoate Aachen solvent; and water, etc. In the middle, 铋 κ κ T is preferably a solvent of water and aromatic hydrocarbons 139604.doc -21 - 201036943 η丨, more preferably a mixed solvent of water and benzene. The use of the solvent is not limited, and from the viewpoint of volume efficiency, it is usually used in an amount of 100 parts by weight or less based on 1 part by weight of the sub-block dihalide (5). The reaction of the fluorenylene didentate (5) with the phenol compound (6) is preferably carried out in the presence of a phase transfer catalyst. Examples of the phase transfer catalyst include a tetrabasic salt of tetra-n-butylammonium bromide, benzyltriethylammonium vaporate, tetra-n-butylammonium sulfate, and trioctylsulfonium ammoxide; A sulphate salt such as a phosphine; and a polyether compound such as 18-crown, polyethylene glycol, etc., preferably a quaternary salt, more preferably butyl ammonium bromide. 1 For the amount of phase transfer catalyst used, the amount of use of the phase transfer catalyst is less than that of the benzene-based compound (6). It is preferably 0.05 to 1 mol. By carrying out the reaction of the sub-(7) with the benzene compound (6) in the presence of an iodine or an iodine compound, the reaction can be carried out more smoothly as a ruthenium compound. Moth metal telluride, etc., preferably ... sodium chlorinated clock, etc. (4) test metal moth compound, more preferably potassium, iodine and iodine compounds are usually used directly by the market. 2. The amount of use of the iodine or iodine compound is preferably 0.01 mol or more relative to the amount of the iodine or iodine compound used in the phenol compound (5). It is 00H mole. The reaction temperature is usually -rc or more, below the boiling point of the solvent, 10~100〇c. 139604.doc •22· 201036943 The reaction can be carried out under normal pressure or under pressure.

The reaction is usually carried out by mixing the sub-denomeric difunctional compound (5) and the benzene-aged compound (6). There is no limitation on the order of mixing, and the sub-denier-based bidentate (5): the benzene-promoting compound (8) and the test may be simultaneously added to the reaction vessel, or may be a mixture of the sub-densate compound (5) and the phenol compound (6). Add a base. A phenolate (6) may also be added to the mixture of the sub-density dentate (5) and the base, or a mixture of the phenol compound (8) and a base may be added to the benzylidene diamide (5). Among them, a method in which a mixture of a benzene-prone compound (6) and a test mixture is added to a benzylidene dihalide (5) is preferred. The progress of the reaction can be confirmed by a usual analytical method such as gas chromatography, high performance liquid chromatography or R. Thus, a reaction mixture containing a benzonitrile di-n-substrate can be obtained, for example, by concentrating the reaction mixture with an aqueous acid solution as needed, followed by concentration to obtain a benzylidene di-formate (1). The obtained benzylidene difunctional compound (1)' can be further purified by a usual purification method such as recrystallization, distillation or column chromatography. Alternatively, the obtained reaction mixture may be used as it is in the above reaction with an alkali metal alkoxide (2). EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples, but the invention is not limited to the examples. Furthermore, the analysis was carried out by the internal standard method of high performance liquid chromatography. Example 1 In a 500 mL round bottom flask, 5,2 g of 2,5-dimethylphenol and 100 mL of toluene were added. To the obtained mixture, 17 weight of 139604.doc -23-201036943% aqueous sodium hydroxide solution was added dropwise at room temperature. The obtained mixture was stirred at 8 ° C for 1 hour and then cooled to 40 ° C to thereby prepare a mixture A. In a separate 500 mL round bottom flask, 2_(chloromethyl)benzylbenzene 76.4 g (content: 98.0% by weight), tetra-n-butylammonium bromide 5·8 g, and toluene 75 mL were added. The aqueous layer of the mixture A prepared in the above-mentioned mixture was added dropwise to the obtained mixture at 40 C over a period of 6 hours, and then the oil layer of the mixture A was added dropwise over 5 hours. After the completion of the dropwise addition, the obtained mixture was shaken at 4 (rc) for 4 hours. The obtained reaction mixture was cooled to room temperature, and a 20% by weight aqueous sulfuric acid solution (4.0 g) was added thereto. The liquid layer was separated, and the obtained organic layer was washed with 153.0 g of water. The obtained organic layer was concentrated under reduced pressure to obtain a crude 2-(2-methyl-p-oxy- decyl) benzyl chloride as a tan solid. 110.9 g. Content: 87.2% by weight. Yield: 91.7% (based on 2-(gasmethyl)benzylbenzene). ^-NMR (CDC13) δ ppm : 2.25 (3H, s), 2.38 (3H, s ), 5.20 (2H, s), 6.76 - 6.81(2H, m), 7.09 (lH, d, J = y.41 Hz), 7.18 (1H, s), 7.41 - 7.54 (3H, m), 7.97 ( 1H} d, J = 7.69 Hz) Melting point: 62 to 65 ° C Example 2 In a 200 mL round bottom flask, 2,5-dimethylphenol 328 hexane and xylene 57 mL were added. To the obtained mixture, 51.3 g of an aqueous solution of sodium oxychloride was added dropwise to a mixture of 2 〇 /. The obtained mixture was allowed to stand at 8 〇 qc for a few hours, and then cooled to 4 (TC), thereby preparing a mixture b. In the other 500 mL round bottom In the bottle, add 2_(chloromethyl)benzylbenzene 139604.doc -24- 201036943 50.0 g (content: 98.0% by weight), 'tetra-n-butylammonium bromide 3.8 g and dimethyl 57 mL. At 40 ° C Next, in the obtained, θ person, "reservation of this compound, the mixture of the above prepared mixture was added dropwise for 6 hours, and the oil layer of the S « was added dropwise for 5 hours. After the completion of the dropwise addition, the obtained mixture was mixed for 4 hours under the thief. The obtained reaction mixture was cooled to the palace, the ® or the μ ^ 丨 main, and the dish was added thereto.

2 2% by weight of sulfuric acid aqueous solution. The obtained mixture was separated, and the obtained organic layer was washed with 100.0 g of water. The obtained organic layer was concentrated under reduced pressure, whereby crude crude 2-(2,5-dimethylphenoxymethyl)benzylbenzene as a tan solid was obtained. Content: 85.5 wt%. Yield: 91.0% (based on 2-(chloromethyl)benzyl chloride). Example 3 In a 200 mL round bottom flask, 2,5-dimethylphenol 19" and 30 mL of toluene were added. To the obtained mixture, 65.5 g of a 1% by weight aqueous sodium hydroxide solution was added dropwise at room temperature. The obtained mixture was stirred at 8 Torr for 1 hour and then cooled to 40 ° C, whereby a mixture was obtained. In a separate 500 mL round bottom flask, 2_(gas methyl), 3 〇.〇 g (content: 98.0% by weight), benzyltriethylammonium hydride 6 g, and toluene 30 mL were added. The aqueous layer of the mixture C prepared above was added dropwise to the obtained mixture at 40 ° C over a period of 6 hours, and then the oil layer of the mixture C was added dropwise over 5 hours. After the end of the dropwise addition, the obtained mixture was vortexed at 40 ° C for 4 hours. The obtained reaction mixture was cooled to room temperature, and 1.7 g of a 20% by weight aqueous sulfuric acid solution was added thereto. The obtained mixture was separated, and the obtained organic layer was washed with water of 139604.doc • 25·201036943 60.0 g. The obtained organic layer was concentrated and reduced under reduced pressure, whereby 39.7 g of crude 2-(2,5-dimethylphenoxymethyl)benzyl chloride as a yellow-color (4) was obtained. Content: 751% by weight. Yield: 72.1% (based on 2-(chloromethyl)benzyl chloride). Example 4 In a 100 mL round bottom flask, 2,5-dimethylphenol 6 35 liter, potassium carbonate 7.66 g, potassium iodide (Μ g and acetonitrile 3 〇 mL) were added at room temperature. 2-(Chloromethyl)benzyl chloride 1 〇〇g (content: 98 〇 wt%) was added dropwise. After the completion of the dropwise addition, the obtained mixture was stirred under 8 Torr for 3 hrs. The mixture was cooled to room temperature, and water (5 Torr) and hydrazine benzene (100 g) were added. The obtained mixture was separated, and the obtained organic layer was washed with water of 2 〇 g. The organic layer obtained was decompressed. Concentrated to obtain 15.3 g of crude 2-(2,5-dimethylphenoxymethyl)thene as a tan solid. Content: 77.5 wt%. Yield: 85.8% (by 2-(gas)曱Base) Benzene gas as a reference) Example 5 In a 500 mL round bottom flask, methanol (188 mL) and 2-(2,5-dianonylphenoxymethyl)benzyl chloride 75.1 g (content: 99.0) were added. % by weight. When heating the obtained solution, the internal temperature is adjusted to 85 °C while discharging a part of the yeast. At the internal temperature of 80-85 ° C, 28 weights are added to the solution over 7 hours. % sodium methoxide / methanol solution 242.9 g. During the dropwise addition, the internal temperature was maintained in the range of 80 to 85 ° C by discharging a part of methanol from the reaction mixture. After the completion of the dropwise addition, the internal temperature was 8 内. The mixture obtained was stirred at ~85 ° C for 139604.doc • 26· 201036943 for 16 hours. The obtained reaction mixture was cooled to an internal temperature of 60 ° C, and 22 mL of difbenzene and 225 mL of water were added. The obtained mixture was separated, and 150.0 g of a 35 wt% aqueous sulfuric acid solution was added to the obtained organic layer. The mixture was stirred at 60 ° C for 2 hours, and 187 mL of diphenylbenzene was added. The obtained mixture was liquid-dissolved under C. The organic layer obtained was cooled to room temperature. The organic layer was washed with a 5 wt% aqueous sodium hydroxide solution of 75 〇g to be washed, and then 15 mL of water was used. The organic layer obtained was concentrated under reduced pressure to give a crude compound of 2-(2,5-dimethylphenoxyfluorenyl)benzaldehyde as a yellow solid (yield: 97.2%). : 98.1% (based on 2-(2,5-dimethylphenoxymethyl)benzyl chloride). Example 6 In a 500 mL round bottom flask, 20.0 mg of 2-(2,5-dimethylphenoxyfluorenyl)benzylidene (content: 95.0% by weight) was added. The internal temperature was 8 〇 to 85 〇c. In the 7 hours of the sound, 28% by weight of sodium bismuth oxide/methanol solution was added dropwise. During the dropwise addition, the internal temperature was maintained at 80 to 85 ° C by discharging a part of methanol. After the addition was completed, the obtained mixture was stirred for 40 hours under ribs. The obtained reaction mixture was cooled to an internal temperature of 6 (rc, added thereto, 7 mL of xylene and 40 mL of water were added. The obtained mixture was separated, and 35 wt% of sulfuric acid was added to the obtained organic layer. The aqueous solution was 4 g. The obtained mixture was stirred at 6 (TC for 2 hours, xylene 23 red was added. The obtained mixture was separated under a machine) and the obtained organic layer was cooled to room temperature. The organic layer was washed with 20.0 g of a 5% by weight aqueous sodium hydroxide solution and 139604.doc -27-201036943 to be washed and then washed with water 40.0 g. The obtained organic layer was concentrated under reduced pressure to obtain a crude solid as a yellow solid. 2_(2,5-Dimethylphenoxymethyl)phenylfurfural 16.2 g. Content: 94.5 wt%. Yield: 99.0% (by 2-(2,5-dimethylphenoxymethyl) Benzene gas is used as a reference.) Example 7 In a 30 mL round bottom flask, 2-(2,5-dimethylphenoxymethane) benzyl chloride 2.0 g (content············· 5 g. Under the internal temperature of 80~85X: under the 7 hours, the weight of the obtained mixture was added dropwise. 2 曱Sodium oxide/methanol dissolved 3.25 g. During the dropwise addition, the internal temperature is maintained in the range of ~85 〇c by discharging a part of methanol from the reaction mixture. After the completion of the dropwise addition, the obtained mixture is stirred at 80 to 85 ° C. I6 hours. The obtained reaction mixture was cooled to an internal temperature of 6 (rc), and 1 mL of diphenylbenzene and 10 mL of water were added thereto. The obtained mixture was separated into 35 wt% of the obtained organic layer. The aqueous solution of sulfuric acid was 4 〇g. The obtained mixture was stirred at 60 ° C for 2 hours, and the obtained mixture was separated by adding diphenylbenzene 1 〇 mL ^ = 60 ° C to cool the obtained organic layer. The organic layer was washed with a 5% by weight aqueous sodium hydroxide solution, and then washed with water (4.0 g). The obtained organic layer was concentrated under reduced pressure to give a crude solid as a yellow solid. (25-methyloxymethyl)benzaldehyde 1.58 g. Content: 94.6 wt%. Yield · 97.1% (based on 2-(2,5-dimercaptophenoxymethyl)benzyl chloride). ... Example 8 Dimethylphenoxymethyl) In a 50 mL round bottom flask, 2_(2,5 139604. Doc -28 · 201036943 5.0 g of chlorine (content: 85.0% by weight) and tetrabutylammonium bromide 23 g. Add 28 weights to the obtained mixture at an internal temperature of 80 to 85 ° C for 7 hours. % sodium methoxide / lysate solution 8.3 3 g. During the dropwise addition, the internal temperature was maintained in the range of 8 〇 85 ° C by discharging a part of methanol from the reaction mixture. The mixture obtained was mixed for 25 hours under ~851. The obtained reaction mixture was cooled to an internal temperature of 60 ° C, and 3 mL of xylene and 25 mL of water were added thereto. The obtained mixture was separated, and a 35 wt% aqueous sulfuric acid solution 丨〇 〇 g was added to the obtained organic layer. The obtained mixture was stirred at 60 ° C for 2 hours, and 22 mL of xylene was added. The obtained mixture was liquid-separated at 6 ° C to cool the obtained organic layer to room temperature. The organic layer was washed with 5 wt% aqueous sodium hydroxide solution 5 〇 g and then washed with water 1 0 · 0 g. The obtained organic layer was concentrated under reduced pressure, whereby a crude 2-(2-5-dimethylphenoxymethyl)benzaldehyde 4.01 g as a yellow solid was obtained. Content: 84.0% by weight. Yield: 97.3% (based on 2-(2,5-dimethylphenoxymethyl) chlorohydrin). Example 9 In a 500 mL round bottom flask, 75.0 g of 2-(2,5-dimethylacetomethoxymethyl)benzylbenzene (content: 99.0 wt.) and methanol (188 mL) were added. The obtained solution was heated, and while the methanol was discharged, the internal temperature was adjusted to 85 °C. Under an internal temperature of 80 to 85 ° C, 282.9 g of a 28 wt% sodium methoxide/decanol solution was added dropwise to the solution over 7 hours. During the dropwise addition, the internal temperature was maintained in the range of 8 Torr to 85 〇c by discharging a part of methanol from the reaction mixture. After the completion of the dropwise addition, the obtained mixture was found at 380,604.doc •29·201036943 for 16 hours at 80 to 85 °C. The obtained reaction mixture was cooled to room temperature, and 78 mL of xylene and 225 mL of water were added thereto. The obtained mixture was separated, and the obtained organic layer was concentrated under reduced pressure to obtain a crude 2-(2,5-monomethyl)methyl phenyl hydrazine as a yellow oil. The base is awakened 73.7 g. Content: 96.3 wt%. Yield: 99.11⁄4 (based on 2-(2,5-diamidinophenoxymethyl)benzyl chloride). 'H-NMR (CDC13) δ ppm : 2.28 (3H, s), 2.36 (3H, s)5 3.38 (6H, s), 5.22 (2H, s), 5.60 (1H, s), 6.73 (1H, d , J = 7.53 Hz), 6.78 (1H, s), 7.07 (1H, d, J = 7.43 Hz), 7.35 - 7.44 (2H, m), 7.63 (1H, s), 7.64 (1H, d, J = 7.29 Hz) Example 1 0 The crude 2-(2,5-dimethylphenoxymethyl)-p-furfural dimethyl acetal obtained in Example 9 73.7 g, xylene 22 11^ and 35 150.0 g of a weight 0/〇 aqueous sulfuric acid solution was mixed. The obtained mixture was stirred at 6 (Γ for 2 hours, and xylene oxime 87 was added thereto at 6 Torr. After the obtained mixture liquid was cooled to room temperature, the obtained organic layer was cooled. It was washed with a 5% by weight aqueous sodium hydroxide solution, and then washed with water i5. The obtained organic layer was concentrated under reduced pressure to give a crude 2-(2,5- Dimethyl phenoxy hydrazino) benzofural 60.5 g. Containing .97.1 weight 1%. Yield: 971% (based on 2_(2,5 dimethylphenoxyfluorenyl)benzyl). Industrial Applicability The intermediate of the present invention can be produced in high yield by reacting the novel compound of the present invention, benzophenone 139604.doc -30-201036943, with an acetal compound in the presence of an acid. More useful benzofuraldehyde compounds.

139604.doc -31 -

Claims (1)

201036943 VII. Patent application scope: 1. A benzaldehyde acetal compound, represented by formula (3) Ο Ο (wherein Q represents a hydrogen atom or a halogen atom, and ^ represents a stupid group which may be substituted with at least one selected from the group consisting of an alkyl group having 1 to 4 carbon atoms and a group of _ atoms, and R represents a carbon number. For! ~ 4 alkyl). For example, the present invention is a compound of the present invention, wherein the ruler is a methyl group. 3. The acetal acetal compound of claim 1 wherein i is a phenyl group substituted with at least one alkyl group having 1 to 4 carbon atoms. 4. The benzaldehyde acetal compound of claim 3, wherein the stupid group substituted with at least one of the substituents having a carbon number of 14 is 2,5-didecylphenyl. 5. An awkward acid-compounding compound according to claim 1, wherein the ruthenium is methyl, ruthenium is 2,5-didecylphenyl, and q is a hydrogen atom. 6. A method for producing a benzofural compound which is produced by the formula (4): (wherein Q represents no hydrogen atom or a _ atom, and ^ represents a phenyl group which may be substituted with at least one selected from the group consisting of a group having a carbon number of 1 to 4 and a dentate atom; 139604.doc 201036943 is characterized by reacting an acetal compound with water in the presence of an acid: "(3) (wherein Q and Ar each represent an alkyl group having the same number as 1 to 4 as described above). Forbearance, R represents carbon as in the manufacture of the benzaldehyde compound of claim 6. Ling, wherein the acid is a cloth tolerance. Among them, the cloth Bennst 8 is a method for producing a benzaldehyde compound according to claim 7 The acid is sulfuric acid. 9. A method for producing a benzaldehyde dialkyl acetal compound, a benzaldehyde dialkyl acetal compound represented by the formula (3): (3) (wherein Q represents a hydrogen atom or a halogen atom, and ^ represents a stupid group which may be substituted with at least one selected from the group consisting of an alkyl group having a carbon number of 1 to 4 and a pixel atom, and R represents a carbon number; An alkyl group of 1 to 4); characterized in that a benzal halide represented by the formula (1) is reacted with an alkali metal alkoxide represented by the formula (2): 139604.doc X201036943 (ι) Ο ίο. 11. 12. 〇13. 14. (wherein Q and Ar respectively represent the same meaning as above, and a halogen atom); 衣不肋一Μ (2) 子) (wherein R represents The same meaning and meaning as defined above, and the method for producing a porphyrin dialkyl acetal compound of claim 9, wherein the subunit group represented by the formula (1) is dilated in the presence of a ruthenium compound. ^Reacting with the test metal oxide oxide represented by the formula (2). For the production method of the benzofuraldehyde dialkyl acetal compound of claim 10, the iodine compound is an alkali metal iodide. A method for producing a benzaldehyde dialkyl acetal compound, wherein: in the presence of a phase transfer catalyst, the metal sulphide represented by the formula (1) and the metal oxidized by the formula (2) are oxidized. The reaction method is as follows: The method for producing a benzoic acid dialkyl acid-reducing compound according to Item 12, wherein the phase transfer catalyst in the pot is a quaternary salt. The sub-unitary bis-compound is represented by the formula (1): Its halogen (1) wherein Q represents a hydrogen atom or a _ atom, and X represents a halogen atom 139604. doc 201036943 Ar represents a substitution by at least one selected from the group consisting of an alkyl group having a carbon number of 1 to 4 and a halogen atom. Phenyl group 15. The benzylidene dihalide of claim 14 wherein the halogen atom is a gas atom 16 - such as a benzidine dihalide of the formula 4, wherein & is at least one carbon number A phenyl group substituted with an alkyl group of 1 to 4. 17. The benzylidene dihalide of claim 16, wherein the phenyl group substituted with at least one alkyl group having 1 to 4 carbon atoms is 2,5-diindenyl Phenyl. 18. As in June, the benzylidene dihalide of Item 14 wherein hydrazine is a chlorine atom, is 2,5-didecylphenyl, and Q is a hydrogen atom. The manufacturing method is to manufacture and produce a benzylidene ditellite compound: (wherein Q and X are characterized by: X and Ar respectively represent the same meaning as described above); The following is the reaction of the phenolic compound of the sub-section represented by the formula (5): the same meaning as described above; (wherein, Q and X respectively represent Ar-〇H 139604.doc 201036943 (wherein Ar represents The method for producing a benzylidene dihalide according to claim 19, wherein a mixture of the phenol compound represented by the formula (6) and a base is added to the formula (5) The reaction is carried out in a benzylidene dihalide. 21. The method for producing a sub-segmented dihalide according to claim 19, wherein in the presence of a phase transfer catalyst, the subunit group II represented by the formula (7) is used. The compound is reacted with a phenol compound represented by the formula (6). Ο 22, a process for producing a benzaldehyde compound, comprising the steps of: (A) a benzylidene dihalide represented by the formula (1) The benzaldehyde monoalkylene condensation compound represented by the formula (3) is obtained by reacting with an alkali metal alkoxide represented by the formula: Ο (wherein Q represents a hydrogen atom or a halogen atom, X represents a halogen atom, and Ar represents a phenyl group which may be substituted with at least one selected from the group consisting of an alkyl group having a carbon number of 1-4 and a halogen atom); RO—(2) (wherein R represents an alkyl group having a carbon number of 1 to 4, and Μ represents an alkali metal atom); 139604.doc 201036943 (wherein Q, Ar and R respectively have the same meanings as described above); and (B) reacting the benzaldehyde acetal compound represented by formula (3) with water in the presence of an acid, Obtaining a benzaldehyde compound represented by the formula (4): (wherein Q and Ar respectively have the same meanings as described above). 23. The method for producing a benzaldehyde compound according to claim 22, which further comprises (C) a benzylidene dihalide represented by the formula (5) and a formula represented by the formula (6) in the presence of a base The step of reacting a phenol compound to obtain a benzylidene dihalide represented by the formula (1): (wherein, Q and X respectively represent the same meanings as described above); Ar—OH (wherein Ar represents the same meaning as described above); (wherein, Q, X and Ar respectively represent the same meanings as described above). 139604.doc 201036943 IV. Designated representative map: (1) The representative representative of the case is: (none). (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: OR 139604.doc