JP2020200287A - Method for producing carbonyl compound - Google Patents

Abstract

To allow a method that oxidizes a first or second alcohol compound to obtain a carbonyl compound to be conducted with a higher yield than that of a method that uses sodium hypochlorite as an oxidizer.SOLUTION: A first or second alcohol compound is oxidized, in the presence of tetraalkylammonium hypochlorite and, preferably, in coexistence with a nitroxy radical catalyst and a metal halide cocatalyst, to produce a carbonyl compound composed of an aldehyde compound, a carboxylic acid compound, and a ketone compound.SELECTED DRAWING: None

Description

The present invention relates to a method for producing a carbonyl compound, specifically, a method for producing a carbonyl compound using a primary or secondary alcohol compound as a reaction raw material and oxidizing the reaction raw material.

Conventionally, it has been known that a primary or secondary alcohol compound is used as a reaction raw material and oxidized to produce a carbonyl compound such as an aldehyde compound, a carboxylic acid compound, or a ketone compound. In order to carry out the above reaction, it is necessary to use an oxidizing agent. For example, sodium hypochlorite is a relatively inexpensive compound, and an aqueous solution thereof is used because the reaction can be easily carried out. (See, for example, Non-Patent Documents 1 and 1 to 4). Further, it is also known that sodium hypochlorite pentahydrate is used instead of sodium hypochlorite to enhance its reactivity (Patent Document 5).
In the oxidation by these sodium hypochlorites, TEMPO (2,2,6,6-tetramethylpiperidin-1-oxyl) and AZADO (2-azaadamantane-N-oxyl) nitroxy radicals are used as catalysts. It is effective to use a catalyst.

P. L. Anelli, et al. , J. Org. Chem. 1987, 52, 2559-2562

Japanese Patent No. 048092229 Japanese Patent No. 04803074 Special Table 2002-511440 Special Table 2006-517584 JP-A-2015-63504

However, the oxidation reaction of the alcohol compound using the sodium hypochlorites is one step more satisfactory in the yield of the obtained carbonyl compound even if the reaction is carried out in combination with the nitroxy radical catalyst. There wasn't. Therefore, it has been required to further enhance the reactivity.

In view of the above problems, the present inventors have continued diligent research in order to develop a method for carrying out the oxidation reaction of the first or second alcohol compound in a high yield. As a result, they have found that the above problems can be solved by proceeding the reaction in the presence of tetraalkylammonium hypochlorite, and have completed the present invention.

That is, the present invention is a method for producing a carbonyl compound, which comprises oxidizing a primary or secondary alcohol compound in the presence of tetraalkylammonium hypochlorous acid.

According to the present invention, the corresponding carbonyl compound can be easily and highly reactively organically synthesized by an oxidation reaction using a primary or secondary alcohol compound as a raw material and tetraalkylammonium hypochlorous acid. By carrying out this reaction in the coexistence of a nitroxy radical catalyst and a metal halide-based co-catalyst as a catalyst, the yield can be further improved, which is extremely useful industrially.

Embodiments of the present invention will be described in detail below. However, the present invention is not limited to these forms.

In the production method of the present invention, a primary or secondary alcohol compound is used as a raw material (hereinafter, also simply abbreviated as "alcohol compound"). As the first or second alcohol compound, known compounds can be applied without particular limitation. These alcohol compounds may be either aliphatic alcohols or aromatic alcohols, but are preferably the general formula (1).

(In the formula, R ¹ is an alkyl group, an aromatic hydrocarbon group, or an alicyclic hydrocarbon group, and R ² is an alkyl group, an aromatic hydrocarbon group, an alicyclic hydrocarbon group, or a hydrogen atom. , R ¹ and R ² may be combined to form an aliphatic hydrocarbon ring)
It is preferably the compound shown by. Here, the alcohol compound becomes a primary alcohol when R ² is a hydrogen atom, and becomes a ^secondary alcohol when R ² is an alkyl group, an aromatic hydrocarbon group, or an alicyclic hydrocarbon group.

In the general formula (1), the alkyl groups of R ¹ and R ² may be linear or branched, and examples thereof include alkyl groups having 1 to 20 carbon atoms. As such alkyl groups, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, neopentyl group, tert-pentyl group. Group, isopentyl group, 2-methylbutyl group, 1-ethylpropyl group, hexyl group, isohexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3- Dimethylbutyl group, 2,2-dimethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1-ethylbutyl group, 2 -Ethylbutyl group, heptyl group, octyl group, nonyl group, decyl group, cetyl group, stearyl group and the like can be mentioned. The alkyl group preferably has 1 to 12 carbon atoms, more preferably 1 to 6 lower alkyl groups, and most preferably a methyl group.

Examples of the aromatic hydrocarbon group include a group having 6 to 20 carbon atoms, and specifically, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a 2-biphenyl group, and the like. Examples thereof include 3-biphenyl group, 4-biphenyl group and terphenyl group, and a phenyl group is particularly preferable.

Further, the alicyclic hydrocarbon group may have, for example, 3 to 20 carbon atoms, preferably 5 to 15, and more preferably 6 to 12. Specifically, monocyclic groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, methylcyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, bicyclo (2,2,1) heptyl group and the like. Arihashi alicyclic group is mentioned, and cyclohexyl group is particularly preferable. Further, these alicyclic groups may be an aromatic hydrocarbon ring or a condensed alicyclic group in which another aliphatic hydrocarbon ring is condensed.

Furthermore, these R ¹ and R ² may be combined to form an aliphatic hydrocarbon ring. Aliphatic hydrocarbon ring such R ¹ and R ² are formed together are spiro ring, and corresponding to the alicyclic hydrocarbon group represented by the R ^1, R ^2, in particular, cycloalkyl A ring, an aromatic ring, or a condensed aliphatic ring in which another aliphatic ring is condensed is preferable.

When R ¹ and R ² are alkyl groups, the alkyl group may have a substituent. Examples of such a substituent include a halogen atom (preferably a chlorine atom), an amino group protected by a protective group, an aromatic hydrocarbon group or an alicyclic hydrocarbon group shown above, and the like. In particular, it is preferably an arylalkyl group in which an aromatic hydrocarbon group is bonded to the terminal carbon.

Further, when R ¹ and R ² are aromatic hydrocarbon groups or alicyclic hydrocarbon groups, these groups may also have substituents, and such substituents include the alkyl groups shown above. , Halogen atom (preferably chlorine atom), thio group, hydroxyl group and the like.

In the method of the present invention, such an alcohol compound is oxidized in the presence of tetraalkylammonium hypochlorous acid to produce a carbonyl compound. If the alcohol compound as the reaction raw material is the primary alcohol, the obtained carbonyl compound is an aldehyde compound in which it is oxidized, for example, the general formula (2).

(In the formula, R ¹ is the same as the general formula (1))
When the oxidation further progresses, at least a part thereof is a carboxylic acid compound, for example, the general formula (3).

(In the formula, R ¹ is the same as the general formula (1))
Replaces with. The extent to which the oxidation reaction remains in the aldehyde compound or proceeds to the carboxylic acid compound depends on the structure of the primary alcohol of the raw material and is not unconditionally determined.

On the other hand, if the alcohol compound as the reaction raw material is a secondary alcohol, it is an oxidized ketone compound, for example, the general formula (4).

(In the formula, R ¹ and R ² are the same as the general formula (1)).
become.

The tetraalkylammonium hypochlorous acid present in the oxidation is preferably one having 1 to 5 carbon atoms such as a methyl group and an ethyl group as the alkyl group. Examples of such tetraalkylammonium hypochlorous acid include tetramethylammonium hypochlorous acid, tetraethylammonium hypochlorite, tetrapropylammonium hypochlorous acid, tetrabutylammonium hypochlorous acid, and the like. Tetramethylammonium chlorate and tetraethylammonium hypochlorous acid are particularly preferred. These tetraalkylammonium hypochlorites can also be used by mixing two or more kinds.

As the tetraalkylammonium hypochlorite, one obtained by any production method may be used. Specifically, chlorination is performed by blowing chlorine gas into a tetraalkylammonium hydroxide solution to produce the target compound. The target compound is eluted by the method or by passing a tetraalkylammonium hydroxide solution through an ion exchange resin to replace it with tetraalkylammonium, and then passing it through a hypochlorite solution such as sodium hypochlorite. The one obtained by the ion exchange resin method is preferable. Derived from these production methods, tetraalkylammonium chloride, tetraalkylammonium hydroxide and the like may coexist in these tetraalkylammonium hypochlorites.

The amount of tetraalkylammonium hypochlorite used is not particularly limited, but is preferably equal to or more than 1 mol with respect to 1 mol of the alcohol compound. From the viewpoint of obtaining the desired carbonyl compound in high yield, it is more preferably 1 to 6 mol, and particularly preferably 1.2 to 5 mol.

As the solvent for carrying out the oxidation reaction of the alcohol compound, an organic solvent for dissolving the raw material compound, in which the organic solvent itself is not easily oxidized by the oxidizing agent tetraalkylammonium hypochlorite, is used. Specifically, halogen-based solvents such as dichloromethane, chloroform, and ethylene dichloride, ester-based solvents such as ethyl acetate and butyl acetate, and aliphatic nitrile solvents such as acetonitrile and pyropionitrile, such as nitrobenzene and benzotrifluoride. , 4-Chlorobenzotrifluoride and other electron-deficient aromatic solvents can be exemplified, preferably halogen-based solvents, and particularly preferably dichloromethane. These may be used by mixing two or more kinds. Further, since the halogen-based solvent dissolves alcohol, an oxidizing agent, etc., 0.5 to 20 mol of water is mixed with a small amount of water, specifically, 1 mol of the halogen-based solvent. Is a preferred embodiment.

A suitable amount of the solvent is an amount that dissolves 0.02 to 0.5 mmol, more preferably 0.03 to 0.4 mmol of the raw material compound in 1 ml of the solvent.

The oxidation reaction of the first or second alcohol compound in the presence of tetraalkylammonium hypochlorous acid is further carried out in the presence of a nitroxy radical catalyst and a metal halide-based co-catalyst. The sex can be greatly enhanced. In particular, the oxidation reaction of the alcohol compound is more reactive in the secondary alcohol than in the primary alcohol. Therefore, in the case of the secondary alcohol, the desired carbonyl compound can be obtained with a high yield to some extent only by the presence of the tetraalkylammonium hypochlorous acid, but in the case of the primary alcohol. In many cases, the target compound cannot be obtained in a sufficient yield, and it is desirable that the nitroxy radical catalyst and the metal halide-based co-catalyst coexist.

As the nitroxy radical catalyst, known free radical compounds having a nitroxy radical moiety can be used without limitation. Specifically, 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO), 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl, 4-methoxy-2, TEMPO-based catalysts such as 2,6,6-tetramethylpiperidin-1-oxyl; 2-azaadamantan-N-hydroxyl (AZADO), 2-azaadamantan-N-oxyl, 1-methyl-2-azaadamantan-N AZADO-based catalysts such as −oxyl, 9-azanor adamantan-N-oxyl, 1,5-dimethyl-9-azanor adamantan-N-oxyl, and azabicyclo [3,3,1] nonane-N-oxyl compounds, etc. In particular, the AZADO-based catalyst is preferable because it has a high activating effect on the oxidation reaction with respect to the primary alcohol. These nitroxy radical catalysts can be used alone or as a mixture of two or more.

The amount of the nitroxyl radical catalyst used may be a so-called catalyst amount, and is usually in the range of 0.00001 to 0.1 mol, preferably 0.001 to 0.01 mol, based on 1 mol of the alcohol compound. used.

On the other hand, the metal halide-based co-catalyst is typically a salt of a halogen atom and an alkali metal or an alkaline earth metal. Examples of suitable metal halides include iodides such as potassium iodide and calcium iodide; bromides such as potassium bromide and calcium bromide; and chlorides such as calcium chloride. Each of these metal halide salts may be used alone or in combination of two or more.

The amount of the metal halide co-catalyst used is not particularly limited, but even if it is used in a large excess, an effect commensurate with the amount used cannot be obtained, and if the amount is too small, a sufficient effect of improving the oxidation reaction can be obtained. Therefore, it is usually used in the range of 0.01 to 10 mol, preferably 0.05 to 2 mol, per 1 mol of the alcohol compound.

As described above, if the oxidation reaction of the alcohol compound of the present invention is carried out in the coexistence of a nitroxy radical catalyst and a metal halide-based co-catalyst in addition to tetraalkylammonium hypochlorite, the reactivity is low. The first alcohol is also useful because its yield can be greatly increased. In particular, in the case of primary alcohols, when an amino alcohol in which an amino group protected by a protecting group is bonded to the carbon at the 2-position of the alkyl alcohol is used as a raw material, it is an intermediate of physiologically active substances such as pharmaceuticals, pesticides and fragrances. It is preferable because it enables high yields of aminoaldehyde and aminocarboxylic acid, which are useful as compounds. The amino alcohol has a structure in which an aromatic hydrocarbon group is bonded to the terminal carbon of the alkyl group, which is excellent in usefulness.

In particular, the general formula (5)

(In the formula, R ³ is an aromatic hydrocarbon group, R ⁴ is an alkyl group, an aromatic hydrocarbon group, an alicyclic hydrocarbon group, or a hydrogen atom, and A is a protective group for an amino group. n is an integer from 1 to 6)
The amino alcohol represented by (1) has an asymmetric carbon atom, and if this is used as a raw material, the general formula (6)

(In the formula, R ³ , R ⁴ , A, and n are the same as the general formula (5)).
Aminoaldehyde represented by and general formula (7)

(In the formula, R ³ , R ⁴ , A, and n are the same as the general formula (5)), and the aminocarboxylic acid represented by the above formula (5) can be obtained, which can be developed as a method for synthesizing an optically active substance and has high value. ..

Here, as the aromatic hydrocarbon groups of R ³ and R ⁴ , the same groups as those represented by R ¹ and R ² of the general formula (1) can be mentioned, and a phenyl group is particularly preferable. Similarly, the alkyl group of R ^4, and also alicyclic hydrocarbon group, the same groups as those shown by R ¹ and R ² in the general formula (1) can be mentioned, and particularly preferably an alkyl group such as a methyl group ..

Further, as the protective group of the amino group represented by A, a known group capable of converting the amino group into an inactive functional group can be appropriately adopted. For example, a methyl group; an allyl group; a tert-butyl group; a benzyl group; p-Nitrobenzyl group; acyl group-based protective group such as acetyl group, pivaloyl group, benzoyl group, trifluoroacetyl group; methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, allyloxycarbonyl group, tert-butoxycarbonyl group , An alkoxycarbonyl group-based protective group such as a benzyloxycarbonyl group; a silyl group-based protective group such as a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, and a tert-butyldiphenylsilyl group; a mesyl group, a tosyl group, p- Examples thereof include a sulfonyl group-based protective group such as a nitrobenzene sulfonyl group and a trifluoromethane sulfonyl group. Of these, a sulfonyl group protecting group is preferable, and a tosyl group is most preferable.

In the general formula (5), n is an integer of 1 to 6, and is particularly preferably 1 to 4.

When an amino alcohol in which an amino group protected by a protecting group is bonded to the carbon at the 2-position of the alkyl alcohol is used as the primary alcohol, the amino alcohol is protected by the carbon at the 2-position and a protecting group. It may have a structure in which an aziridine ring is formed between the nitrogen atom of the amino group formed therein. Even if the oxidation reaction of the alcohol proceeds, the aziridine ring is maintained well, and the corresponding aziridine ring-containing aldehyde and carboxylic acid can be obtained in good yield. Therefore, this method is also applicable and useful as a method for synthesizing an optically active substance. Specifically, the general formula (8)

(In the formula, R ⁵ is an alkyl group, an aromatic hydrocarbon group, an alicyclic hydrocarbon group, or a hydrogen atom, and A is a protective group for an amino group.)
Using the aziridine ring-containing alcohol represented by the above, the general formula (9)

(Wherein, ^{R 5} and A are the same as defined above, and the formula (8))
Aziridine ring-containing aldehyde represented by and general formula (10)

(Wherein, ^{R 5} and A are the same as defined above, and the formula (8))
This is a reaction for obtaining an aziridine ring-containing carboxylic acid represented by.

The above oxidation reaction is usually carried out under stirring at a reaction temperature of 0 to 50 ° C., preferably at a reaction temperature of 0 to 35 ° C. Setting the reaction temperature to 60 ° C. or higher is not preferable because it causes a competitive reaction between the decomposition reaction of tetraalkylammonium hypochlorous acid and the oxidation reaction and increases the amount of tetraalkylammonium hypochlorous acid used. Lowering the reaction temperature to a low temperature (less than 0 ° C.) at which the reaction system does not solidify requires special equipment measures and causes a decrease in the reaction rate, which is rather less advantageous.

The reaction time is usually selected from the range of 0.2 to 8 hours, more preferably 0.5 to 4 hours.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.

Example 1
Using 0.62 ml of ethyl acetate as a solvent, 0.5 mmol of 1-phenylethanol, which is a secondary alcohol, 1 mmol of tetramethylammonium hypochlorous acid, and 1 mmol of acetic acid were charged, and the mixture was reacted by stirring at room temperature for 2 hours. ..

The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that acetophenone was obtained in a yield of 78%.

Example 2
The procedure was the same as in Example 1 except that tetraethylammonium hypochlorite was used instead of tetramethylammonium hypochlorite. The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that acetophenone was obtained in a yield of 89%.

Comparative Example 1
The procedure was the same as in Example 1 except that sodium hypochlorite pentahydrate was used instead of tetramethylammonium hypochlorite. The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that acetophenone was obtained in a yield of 57%.

Example 3
In a solvent of 1.3 ml of dichloromethane and 2.7 ml of water, 0.5 mmol of the primary alcohol, octyl alcohol, 1.25 mmol of tetramethylammonium hypochlorous acid, 2,2,6,6-tetramethylpiperidine- The reaction was carried out by charging 0.005 mmol of 1-oxyl and 0.05 mmol of potassium bromide and stirring at room temperature for 15 hours. The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that octanic acid was obtained in a yield of 32% and octylaldehyde was obtained in a yield of 15%.

Example 4
The procedure was the same as in Example 3 except that 2-hydroxy-2-azaadamantane was used instead of 2,2,6,6-tetramethylpiperidine-1-oxyl and the mixture was stirred at room temperature for 23 hours. The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that octanoic acid was obtained in a yield of 87%.

Example 5
The procedure was the same as in Example 4 except that tetraethylalkylammonium hypochlorite was used instead of tetramethylammonium hypochlorite. The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that octanoic acid was obtained in a yield of 78%.

Comparative Example 2
The procedure was the same as in Example 5 except that sodium hypochlorite pentahydrate was used instead of tetraethylammonium hypochlorite. The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that octanic acid was obtained in a yield of 12% and octylaldehyde was obtained in a yield of 5%.

Example 6
In a solvent of 1.3 ml of dichloromethane and 2.7 ml of water, 0.5 mmol of benzyl alcohol, 1.75 mmol of tetramethylammonium hypochlorous acid, 0.005 mmol of 2-hydroxy-2-azaadamantane, 0.05 mmol of potassium bromide. The reaction was carried out by charging and stirring at room temperature for 24 hours. The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that benzoic acid was obtained in a yield of 62% and benzaldehyde was obtained in a yield of 26%.

Example 7
The procedure was the same as in Example 6 except that pentyl alcohol was used as the primary alcohol instead of benzyl alcohol. The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that pentanoic acid could be obtained in a yield of 95%.

Example 8
The same procedure as in Example 6 was carried out except that hexyl alcohol was used as the primary alcohol instead of benzyl alcohol. The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that the yield of caproic acid was 83% and that hexylaldehyde was slightly detected.

Example 9
The same procedure as in Example 6 was carried out except that dodecyl alcohol was used as the primary alcohol instead of benzyl alcohol. The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that dodecanoic acid was obtained in a yield of 95%.

Example 10
In a solvent of 0.62 ml of ethyl acetate, 0.25 mmol of (2-methyl-1-tosylaziridin-2-yl) methanol, 0.6 mmol of tetramethylammonium hypochlorous acid, 2-hydroxy-2-azaadamantan 0. The reaction was carried out by charging .0025 mmol and 0.025 mmol of potassium bromide and stirring at 0 ° C. for 6.5 hours. From the obtained reaction solution, (2-methyl-1-tosylaziridin-2-yl) carboxylic acid was isolated in a yield of 89%. The obtained (2-methyl-1-tosylaziridin-2-yl) carboxylic acid was identified from the following data measured by ¹ H-NMR.
^{1 1} H-NMR (400 MHz, CDCl ₃ ): δ1.95 (s, 3H), 2.46 (s, 3H), 2.70 (s, 1H), 2.84 (s, 1H), 7.36 (D, J = 8.3Hz, 2H), 7.85 (d, J = 8.3Hz, 2H).
Example 11
In a solvent of 0.62 ml of ethyl acetate, 0.25 mmol of (2-methyl-1-tosylaziridin-2-yl) methanol, 0.3 mmol of tetramethylammonium hypochlorous acid, 2-hydroxy-2-azaadamantan 0. The reaction was carried out by charging .0025 mmol and 0.025 mmol of potassium bromide and stirring at 0 ° C. for 6.5 hours. From the obtained reaction solution, (2-methyl-1-tosylaziridin-2-yl) carboxylic acid was isolated in a yield of 45%. Together, (2-methyl-1-tosylaziridin-2-yl) carboaldehyde was obtained in 14% yield. The obtained (2-methyl-1-tosylaziridin-2-yl) carboaldehyde was identified from the following data measured by ¹ H-NMR.
^{1 1} H-NMR (400 MHz, CDCl ₃ ): δ1.69 (s, 3H), 2.46 (s, 3H), 2.84 (s, 1H), 2.88 (s, 1H), 7.36 (D, J = 8.8Hz, 2H), 7.85 (d, J = 8.2Hz, 2H), 9.07 (s, 1H).
Example 12
In a solvent of 0.62 ml of dichloromethane, 0.25 mmol of 2-methyl-3-phenyl-2-tosylamino-1-propyl alcohol, 0.3 mmol of tetramethylalkylammonium hypochlorite, 2-hydroxy-2-azaadamantan The reaction was carried out by charging 0.0025 mmol and 0.025 mmol of potassium bromide and stirring at 0 ° C. for 17.5 hours. The product of the obtained reaction solution was measured by ¹ H-NMR, and it was confirmed that 2-methyl-3-phenyl-2-tosylamino-1-propylaldehyde could be obtained in a yield of 67%. The obtained 2-methyl-3-phenyl-2-tosylamino-1-propylaldehyde was identified from the following data measured by ¹ H-NMR.
^{1 1} H-NMR (400 MHz, CDCl ₃ ): δ1.30 (s, 3H), 2.41 (s, 3H), 3.08 (d, J = 14.1 Hz, 1H), 3.11 (d, J = 13.7Hz, 1H), 5.13 (s, 1H), 7.14-7.31 (m, 7H), 7.71 (d, J = 8.3Hz, 2H), 9.47 ( s, 1H).

Claims (10)

A method for producing a carbonyl compound, which comprises oxidizing a primary or secondary alcohol compound in the presence of tetraalkylammonium hypochlorous acid. The carbonyl according to claim 1, wherein the oxidation of the primary or secondary alcohol compound in the presence of tetraalkylammonium hypochlorous acid is further carried out in the presence of a nitroxy radical catalyst and a metal halide-based co-catalyst. Method for producing a compound. The method for producing a carbonyl compound according to claim 1, wherein the primary alcohol compound is oxidized to produce an aldehyde compound and / or a carboxylic acid compound. The method for producing a carbonyl compound according to claim 3, wherein the primary alcohol is an amino alcohol in which an amino group protected by a protecting group is bonded to the carbon at the 2-position of the alkyl alcohol. The method for producing a carbonyl compound according to claim 4, wherein the alkyl alcohol has a structure in which an aromatic hydrocarbon group is bonded to the terminal carbon of the alkyl group. An amino alcohol in which an amino group protected by a protecting group is bonded to the carbon at the 2-position of the alkyl alcohol forms an aziridine ring between the carbon at the 2-position and the nitrogen atom of the amino group protected by the protecting group. The method for producing a carbonyl compound according to claim 4, which is a formed structure. The method for producing a carbonyl compound according to any one of claims 4 to 6, wherein the protecting group for the amino group is a tosyl group. The method for producing a carbonyl compound according to any one of claims 1 to 7, wherein the tetraalkylammonium hypochlorite is tetramethylammonium hypochlorite or tetraethylammonium hypochlorite. In any one of claims 2 to 8, the nitroxy radical catalyst is a 2,2,6,6-tetramethylpiperidin-1-oxyl-based catalyst or a 2-azaadamantane-N-oxyl compound-based catalyst. The method for producing a carbonyl compound according to the above. The method for producing a carbonyl compound according to any one of claims 2 to 9, wherein the metal halide-based cocatalyst is potassium bromide.