JP4052703B2 - Method for producing alcohols - Google Patents

Description

[0001]
[Industrial application fields]
The invention of this application relates to a process for producing alcohols that can hydrogenate carbonyl compounds to alcohols useful as synthetic intermediates for pharmaceuticals, agricultural chemicals or many general-purpose chemicals in high yield and at high speed. .
[0002]
[Prior art and its problems]
It is well known to produce the corresponding alcohols by hydrogenation of carbonyl compounds using homogeneous catalysts. For example, (1) Comprehensive Organometallic Chemistry, Vol. 4, page 931 (1982), Eds. G. Wilkinson, FGAStone and EWAbel, using a ruthenium complex, (2) Inorg, Nucl. Chem. Rhodium described in J. Organomet. Chem., Vol. 129, 239 (1977); Chem. Letters, 261 (1982) and Tetrahedron Letters, Vol. 35, 4963 (1994). A method using a complex, (3) a method using an iridium complex described in J. Am. Chem. Soc., Vol. 115, page 3318 (1993), and the like are known. Further, a method of hydrogenation in the presence of a phosphine and a diamine ligand described in (4) J. Am. Chem. Soc., Vol. 117, pages 2675-2676 (1995) is also known.
[0003]
However, these conventional methods have a problem that the hydrogenation activity of the complex catalyst is low and a relatively high temperature or a high hydrogen pressure is required, so that it is not necessarily suitable for practical use. Furthermore, although the method described in the above (4) is excellent in selectivity and activity, it uses a phosphine-ruthenium complex, so it is not particularly safe from the viewpoint of toxicity, and industrially. There was also a difficulty in collecting and using.
[0004]
Therefore, the invention of this application overcomes the drawbacks in the prior art, provides an extremely high activity catalyst system using an inexpensive and practical ruthenium complex, and a method for producing alcohols using this catalyst system The purpose is to provide.
[0005]
[Means for Solving the Problems]
That is, the invention of this application is characterized by the following in order to solve the above problems.
First: In a liquid reaction medium, the following formula RuX _m L _n
(In the formula, X represents a hydrogen atom, a halogen atom, a carboxyl group, a hydroxy group, or an alkoxy group, L represents an olefin ligand or an aromatic compound ligand, and m and n are each 1 to 1) A transition metal catalyst represented by general formula NR ³ R ⁴ R ⁵ , a primary amine or a secondary amine represented by general formula NR ³ R ⁴ R ⁵ , and general formula NR ⁶ R ⁷ N—Z—NR ⁸ Diamines represented by R ⁹ (R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group, an allyl group, Or an aryl group, wherein Z represents an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group, or an aryl group.) A carbonyl compound in the presence of at least one nitrogen-containing organic compound, a base, and gaseous hydrogen It is reacted with gaseous hydrogen corresponding Al Method for producing an alcohol, which comprises hydrogenating the Lumpur acids.
2: The ligand L of the transition metal catalyst is a method for producing the first alcohol, which is an olefinic cyclic compound.
Third: The method for producing the second alcohol, wherein the olefinic cyclic compound is cyclohexene, 1,3-cyclohexadiene, 1,5-cyclooctadiene, cyclooctatriene, or norbonadiene.
Fourth: The method for producing the first alcohol, wherein the ligand L of the transition metal catalyst is benzene, p-cymene, mesitylene, naphthalene, or anthracene.
5 : The method for producing any one of the first to fourth alcohols, wherein the base is a hydroxide or salt of an alkali metal or alkaline earth metal, or a quaternary ammonium salt.
Sixth : The carbonyl compound is represented by the general formula:
(In the formula, R ¹ and R ² are a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group or a heterocyclic group, or RO— or RO—CO—, and R has a substituent. R ¹ and R ² may be bonded to form a ring, provided that R ¹ and R ² do not both become a halogen atom. The method for producing any one of the first to fifth alcohols represented by:
[0007]
DETAILED DESCRIPTION OF THE INVENTION
The invention of this application has the features as described above. Hereinafter, this embodiment will be described in detail.
First, a carbonyl compound as a raw material compound for the production of alcohols may be any compound having a carbonyl group (—CO—).
[Chemical 2]
[0009]
(In the formula, R ¹ and R ² are a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group or a heterocyclic group, or RO— or RO—CO—, and R has a substituent. And R ¹ and R ² may be bonded to form a ring, but R ¹ and R ² are not both halogen atoms. Is shown).
[0010]
Hydrocarbon groups include alkyl groups, alkenyl groups, cycloalkyl groups, cycloalkenyl groups, aryl groups, aralkyl groups, and heterocyclic groups also include furyl groups, chenyl groups, imidazole groups, piperidyl groups, pyridines. Various groups such as a group and a carbazole group may be used.
Specifically, in the carbonyl compound represented by the general formula (a), R ¹ and R ² may be the same or different, and R ¹ and R ² may be bonded to form a ring. Specifically, in R ¹ and R ² , a halogen atom is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like, and an alkyl group is, for example, a methyl group, an ethyl group, or an n-propyl group , Isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-amyl group, neopentyl group, n-hexyl group, cyclohexyl group, n-octyl group, n-nonyl group, menthyl group, 2,3, 4-trimethyl-3-pentyl group, 2,4-dimethyl-3-pentyl group, etc., as the aralkyl group, benzyl group, 2-phenylethyl group, 2-naphthylethyl group, diphenylmethyl group As an aryl group, a phenyl group, a naphthyl group, a biphenyl group, a furyl group, a thiophenyl group, etc., and as an alkenyl group, a 2-methyl-1-propenyl group, a 2-butenyl group, a trans-β-styryl group, 3-phenyl-1-propenyl group, 1-cyclohexenyl group, etc., alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, t-butoxy group, etc., aryloxy groups such as phenoxy group are alkyl groups Examples of the oxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a t-butyloxycarbonyl group, a benzyloxycarbonyl group, and a phenyloxycarbonyl group. When these groups are further substituted with a substituent, examples of the substituent include the same halogen atom as described above, the same alkoxyl group as described above, the same aryloxy group as described above, a methyl group, an ethyl group, Lower alkyl groups such as isopropyl group, n-butyl group, t-butyl group, n-amyl group and n-hexyl group, lower alkylthio groups such as n-propylthio group and t-butylthio group, arylthio groups such as phenylthio group, Examples thereof include a nitro group and a hydroxyl group.
[0011]
In this invention, a ternary catalyst system of a nitrogen-containing organic compound base containing a homogeneous hydrogenation catalyst is used for hydrogenation of such a carbonyl compound. Among these, a homogeneous hydrogenation catalyst is liquid under reaction conditions. complexes of Ru (ruthenium) that are solubilized in the reaction medium is used effectively.
[0012]
When the show Le ruthenium complex catalyst, the following equation [0013]
[Chemical 3]
[0014]
( X represents a hydrogen atom, a halogen atom, a carboxyl group, a hydroxy group, or an alkoxy group, L represents an olefin ligand or an aromatic compound ligand, and m and n are integers of 1 to 6, respectively. are shown.) are shown ones.
Examples of L: olefin ligand in the ruthenium complex represented by the formula RuX _m L _n include, for example, ethylene, allyl, butadiene, cyclohexene, 1,3-cyclohexadiene, 1,5-cyclooctadiene, cyclooctatriene, Examples include norbornadiene, acrylic acid ester, methacrylic acid ester, cyclopentadienyl, pentamethylcyclopentadienyl, and the like. Further, examples of the cyclic compound include a monocyclic or polycyclic compound that can be represented by the following formula.
[0015]
[Formula 4]
[0016]
R _{1 to} R ₅ are composed of the same or different substituents, and have, for example, a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or a substituent. An aryl group which may be substituted, an alkenyl group which may have a substituent, an alkoxyl group which may have a substituent, or an alkyloxycarbonyl group. Specifically, the halogen atom is a fluorine atom, chlorine atom, bromine atom, iodine atom, etc., and the alkyl group is, for example, a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group. , T-butyl group, n-amyl group, neopentyl group, n-hexyl group, cyclohexyl group, n-octyl group, n-nonyl group, menthyl group, 2,3,4-trimethyl-3-pentyl group, 2, 4-dimethyl-3-pentyl group and the like include benzyl group, 2-phenylethyl group, 2-naphthylethyl group, diphenylmethyl group and the like as aralkyl groups, and phenyl group, naphthyl group, biphenyl group, furyl as aryl groups Group, thiophenyl group, etc., as alkenyl group, 2-methyl-1-propenyl group, 2-butenyl group, trans-β-styl Group, 3-phenyl-1-propenyl group, 1-cyclohexenyl group, etc., alkoxy groups include methoxy group, ethoxy group, n-propoxy group, t-butoxy group, etc., aryloxy groups include phenoxy group, etc. However, examples of the alkyloxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a t-butyloxycarbonyl group, a benzyloxycarbonyl group, and a phenyloxycarbonyl group. When these groups are further substituted with a substituent, examples of the substituent include the same halogen atom as described above, the same alkoxyl group as described above, the same aryloxy group as described above, a methyl group, an ethyl group, Lower alkyl groups such as isopropyl group, n-butyl group, t-butyl group, n-amyl group and n-hexyl group, lower alkylthio groups such as n-propylthio group and t-butylthio group, arylthio groups such as phenylthio group, Examples thereof include a nitro group and a hydroxyl group. The number of the substituents is any number from 1 to 5, and the place can be selected arbitrarily.
[0017]
The Fang aromatic compound ligand, benzene, p- cymene, mesitylene, hexamethylbenzene, naphthalene, although anthracene are exemplary, aromatic compounds that can be further ligands can be represented by the following formula It is a monocyclic or polycyclic aromatic compound.
[0018]
[Chemical formula 5]
[0019]
R ^{a to} R ^f are composed of the same or different substituents, and can represent, for example, hydrogen, a saturated or unsaturated hydrocarbon group, an allyl group, or a functional group containing a different atom. For example, alkyl groups such as methyl, ethyl, propyl, butyl, t-butyl, pentyl, hexyl, heptyl, cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., benzyl, vinyl, allyl, phenyl, naphthyl, etc. A functional group containing a hetero atom such as a group such as a saturated hydrocarbon, a hydroxyl group, an alkoxy group, or an alkoxycarbonyl group can be shown. The number of the substituents is any number from 1 to 6, and the location can be selected arbitrarily.
[0022]
For example, examples of ruthenium complexes as starting materials include ruthenium chloride (III) hydrate, ruthenium bromide (III) hydrate, ruthenium iodide (III) hydrate and other inorganic ruthenium compounds, [ruthenium dichloride] (Norbornadiene)] polynuclear, [ruthenium dichloride (cyclooctadiene)] ruthenium compounds coordinated with diene, [ruthenium dichloride (benzene)] dinuclear, [ruthenium dichloride (p-cymene) ] A ruthenium complex in which an aromatic compound such as a binuclear body, [ruthenium dichloride (trimethylbenzene)] dinuclear body, or [ruthenium dichloride (hexamethylbenzene)] binuclear body is coordinated is used. In addition, a ruthenium complex having a diamine ligand or a ligand that can be substituted with a diamine ligand is not particularly limited to the above. For example, various ruthenium complexes shown in COMPREHENSIVE ORGANOMETALIC CHEMISTRY II Vol.7, pages 294-296 can be used as starting materials.
[0023]
The ruthenium complex has high activity. The amount of the ruthenium complex used varies depending on the reaction vessel and economy, but can be used at a molar ratio of 1/100 to 1 / 100,000 with respect to the carbonyl compound as the reaction substrate, preferably 1/200 to 1 The range is / 10,000.
[0024]
The base used in the present invention is represented by, for example, the general formula MY, where M is an alkali metal or alkaline earth metal, and Y is a hydroxyl group, an alkoxy group, a mercapto group, or a naphthyl group. Specific examples thereof include KOH, KOCH ₃ , KOCH (CH ₃ ) ₂ , KC ₁₀ H ₈ , LiOH, LiOCH ₃ , LiOCH (CH ₃ ) _{2 and the} like. Furthermore, quaternary ammonium salts can be used as well.
[0025]
The usage-amount of said base is 0.5-100 equivalent with respect to a ruthenium complex , Preferably 2-40 equivalent is desirable. Further, in the present invention, a nitrogen-containing organic compound is used in the reaction system. In this case, typical examples of the nitrogen-containing organic compound include amines, amine derivatives, nitriles, isocyanides, and the like. Derivatives are mentioned as suitable.
[0026]
Amine compounds suitable for use may diamine represented by the general formula NR ³ R ⁴ primary amine or secondary amine represented by R ⁵ or the general formula ^{NR 6 R 7 N-Z-} NR 8 R 9,. Here, (R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ are, for example, carbon atoms such as hydrogen or alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups, allyl groups, aryl groups, The same or different hydrogen groups may be formed to form a cyclic amine, and Z represents a group selected from hydrocarbon groups such as an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group, and an aryl group. Examples include ammonia, methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, cyclopentylamine, cyclohexylamine, benzylamine, dimethylamine, diethylamine, dipropylamine, dihexylamine, dicyclopentylamine, dicyclohexylamine, Dibenzylamine, diphenylamine, phenylethylamine, Monoamine compounds such as lysine and piperazine, methylenediamine, ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,4-diaminobutane, 2,3-diaminobutane, 1,2-cyclopentanediamine, 1,2-cyclohexanediamine, N-methylethylenediamine, N, N′-dimethylethylenediamine, N, N, N′-trimethylethylenediamine, N, N, N ′, N′-tetramethylethylenediamine, o-phenylenediamine, p -A diamine compound such as phenylenediamine is exemplified.
[0027]
The amount of these compounds used is 1 to 20 equivalents in the case of a monoamine compound, more preferably 2 to 8 equivalents relative to the ruthenium complex , and 0.5 to 20 equivalents in the case of a diamine compound, preferably 1 to 6 equivalents. Range. In the reduction reaction of the present invention, addition of these amine compounds is essential, and when not added as described in Comparative Examples, the yield of the reduction product is extremely reduced.
[0028]
In the method of the present invention, the liquid solvent can be appropriately used as long as it can solubilize the reaction raw material and the catalyst system. Examples thereof include aromatic solvents such as toluene and xylene, aliphatic solvents such as pentane and hexane, halogen-containing hydrocarbon solvents such as methylene chloride, ether solvents such as ether and tetrahydrofuran, methanol, ethanol, 2-propanol, Alcohol solvents such as butanol and benzyl alcohol, and organic solvents containing heteroatoms such as acetonitrile, DMF, N-methylpyrrolidone, pyridine and DMSO can be used. Alcohol solvents are preferred because the reaction product is an alcohol. These liquid solvents can be used alone, but can also be used as a mixed solvent among them.
[0029]
The amount of solvent is determined by the solubility and economics of the reaction substrate. In the case of 2-propanol, the substrate concentration can be as low as 1% or less and close to the solvent-free state of the substrate alone, but preferably 20 to 50% by weight.
The hydrogen pressure in the method of the present invention is in the range of 1 to 200 atmospheres, preferably 3 to 100 atmospheres.
[0030]
The reaction temperature is preferably from 15 ° C. to 100 ° C. in consideration of economy, but the reaction can be carried out at a room temperature of 25-40 ° C. However, the present invention is characterized in that the reaction proceeds even at a low temperature of −30 to 0 ° C. The reaction time varies depending on the reaction conditions such as reaction substrate concentration, temperature, pressure and the like, but the reaction is completed in several minutes to 10 hours.
[0031]
The reaction can be carried out regardless of whether the reaction mode is batch or continuous.
[0032]
【Example】
Hereinafter, the present invention will be described in more detail with reference to examples.
Example 1
[RuCl ₂ (cod)] ₂ (2.8 mg, 0.01 mmol), KOH (0.04 mmol), ethylenediamine (0.02 mmol), benzophenone (91 mg, 5.0 mmol), 10 mo 2-propanol and 2 ml toluene After dissolving in 100 μl of DMF, degassing and purging with argon, the whole amount was transferred to a 100 ml metal autoclave and then charged with hydrogen to a predetermined pressure (40 atm) to start the reaction.
[0033]
After stirring the reaction solution for 3 hours, the reaction pressure was returned to normal pressure, and the product benzhydrol was analyzed by TLC monitor (silica gel: n-hexane / ethyl acetate = 4/1), high performance liquid chromatography and NMR. Was identified and quantified. All of the reaction substrate was consumed and the product yield was over 99%.
Example 2
[RuCl ₂ (cod)] ₂ (2.8 mg, 0.01 mmol), KOH (0.04 mmol), ethylenediamine (0.02 mmol) and 2-chlorobenzophenone (1.083 g, 5.0 mmol) in 10 mo 2- After dissolving in propanol, 2 ml of toluene and 100 μl of DMF, deaeration and purging with argon, the whole amount was transferred to a 100 ml metal autoclave, and then hydrogen was charged to a predetermined pressure (40 atm) to start the reaction.
[0034]
After stirring the reaction solution for 3 hours, the reaction pressure was returned to normal pressure, and the product benzhydrol was analyzed by TLC monitor (silica gel: n-hexane / ethyl acetate = 4/1), high performance liquid chromatography and NMR. Was identified and quantified. All of the reaction substrate was consumed and the product yield was over 97%.
Example 3
[RuCl ₂ (cod)] ₂ (2.8 mg, 0.01 mmol), KOH (0.04 mmol), 1,2-diphenylethylenediamine (0.02 mmol) and 2,4′-dichlorobenzophenone (1.255 g, 5.0 mmol) was dissolved in 10 ml of 2-propanol, 2 ml of toluene and 100 μl of DMF, deaerated, purged with argon, transferred to a 100 ml metal autoclave, and then charged with hydrogen to a predetermined pressure (40 atm). Started.
[0035]
After stirring the reaction solution for 3 hours, the reaction pressure was returned to normal pressure, and the product benzhydrol was analyzed by TLC monitor (silica gel: n-hexane / ethyl acetate = 4/1), high performance liquid chromatography and NMR. Was identified and quantified. All of the reaction substrate was consumed and the product yield was over 96%.
Example 4
[RuCl ₂ (p-cymene)] ₂ (6.1 mg, 0.01 mmol), KOH (0.04 mmol), 1,2-diphenylethylenediamine (0.02 mmol) and 4-chlorobenzophenone (1.083 g, 5. 0 mmol) was dissolved in 10 ml of 2-propanol and 2 ml of toluene, degassed and purged with argon, and the whole amount was transferred to a 100 ml metal autoclave, and then hydrogen was charged to a predetermined pressure (40 atm) to start the reaction.
[0036]
After stirring the reaction solution for 3 hours, the reaction pressure was returned to normal pressure, and the product benzhydrol was analyzed by TLC monitor (silica gel: n-hexane / ethyl acetate = 4/1), high performance liquid chromatography and NMR. Was identified and quantified. All of the reaction substrate was consumed and the product yield was 98%.
Example 5
[RuCl ₂ (p-cymene)] ₂ (6.1 mg, 0.01 mmol), KOH (0.04 mmol), 1,2-diphenylethylenediamine (0.02 mmol) and acetophenone (0.601 g, 5.0 mmol). It was dissolved in 10 ml of 2-propanol, 2 ml of toluene and 100 μl of DMF, degassed and purged with argon, then transferred to a 100 ml metal autoclave, and then charged with hydrogen to a predetermined pressure (40 atm) to start the reaction.
[0037]
After stirring the reaction solution for 3 hours, the reaction pressure was returned to normal pressure, and the reaction solution was identified and quantified by 1-phenylethanol as a product by gas chromatography, high performance liquid chromatography and NMR. All of the reaction substrate was consumed and the product yield was 98%.
Example 6
[RuCl ₂ (p-cymene)] ₂ (6.1 mg, 0.01 mmol), KOH (0.04 mmol), 1,2-diphenylethylenediamine (0.02 mmol), and cyclohexanone (0.491 g, 5.0 mmol). It was dissolved in 10 ml of 2-propanol, 2 ml of toluene and 100 μl of DMF, degassed and purged with argon, then transferred to a 100 ml metal autoclave, and then charged with hydrogen to a predetermined pressure (40 atm) to start the reaction.
[0038]
After stirring the reaction solution for 3 hours, the reaction pressure was returned to normal pressure, and the reaction solution was identified and quantified by gas chromatography, high performance liquid chromatography, and NMR. All of the reaction substrate was consumed and the product yield was 95%.
Example 7
[RuCl ₂ (p-cymene)] ₂ (6.1 mg, 0.01 mmol), KOH (0.04 mmol), 1,2-diphenylethylenediamine (0.02 mmol) and 2-octanone (0.641 g, 5.0 mmol) ) Was dissolved in 10 ml of 2-propanol and 2 ml of toluene, deaerated and purged with argon, and the whole amount was transferred to a 100 ml metal autoclave, and then hydrogen was charged to a predetermined pressure (40 atm) to start the reaction.
[0039]
After stirring the reaction solution for 3 hours, the reaction pressure was returned to normal pressure, and the reaction solution was identified and quantified by gas chromatography, high performance liquid chromatography, and NMR. All of the reaction substrate was consumed and the product yield was 95%.
Comparative Example 1
[RuCl ₂ (cod)] ₂ (2.8 mg, 0.01 mmol), KOH (0.04 mmol) and benzophenone (91 mg, 5.0 mmol) were dissolved in 10 ml of 2-propanol and 2 ml of toluene, degassed, After the replacement, the whole amount was transferred to a 100 ml metal autoclave, and then hydrogen was charged to a predetermined pressure (40 atm) to start the reaction. After the reaction solution was stirred for 18 hours, the reaction pressure was returned to normal pressure, and the product benzhydrol was analyzed by TLC monitor (silica gel: n-hexane / ethyl acetate = 4: 1), high performance liquid chromatography and NMR. Was identified and quantified. 97% of the reaction substrate remained, and the yield of the product was 3% or less.
[0040]
【The invention's effect】
As described in detail above, the invention of this application makes it possible to efficiently produce alcohols by using an inexpensive and practical, highly active ruthenium catalyst.

Claims (6)

In the liquid reaction medium, the following formula RuX _m L _n
(In the formula, X represents a hydrogen atom, a halogen atom, a carboxyl group, a hydroxy group, or an alkoxy group, L represents an olefin ligand or an aromatic compound ligand, and m and n are each 1 to 1) A transition metal catalyst represented by general formula NR ³ R ⁴ R ⁵ , a primary amine or a secondary amine represented by general formula NR ³ R ⁴ R ⁵ , and general formula NR ⁶ R ⁷ N—Z—NR ⁸ Diamines represented by R ⁹ (R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group, an allyl group, Or an aryl group, wherein Z represents an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group, or an aryl group.) A carbonyl compound in the presence of at least one nitrogen-containing organic compound, a base, and gaseous hydrogen It is reacted with gaseous hydrogen corresponding Al Method for producing an alcohol, which comprises hydrogenating the Lumpur acids.   The method for producing an alcohol according to claim 1, wherein the ligand L of the transition metal catalyst is an olefinic cyclic compound.   The method for producing an alcohol according to claim 2, wherein the olefinic cyclic compound is cyclohexene, 1,3-cyclohexadiene, 1,5-cyclooctadiene, cyclooctatriene, or norbonadiene.   The method for producing an alcohol according to claim 1, wherein the ligand L of the transition metal catalyst is benzene, p-cymene, mesitylene, naphthalene, or anthracene. 5. The method for producing an alcohol according to claim 1, wherein the base is an alkali metal or alkaline earth metal hydroxide or salt, or a quaternary ammonium salt. Carbonyl compounds are represented by the general formula
(Wherein R ¹ , R ² Is a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group or heterocyclic group, or RO- or RO-CO-, wherein R is an optionally substituted hydrocarbon group or Represents a heterocyclic group, R ¹ And R ² May be bonded to form a ring, provided that R ¹ And R ² Indicates that they are not halogen atoms. The method for producing an alcohol according to any one of claims 1 to 5 represented by: