JPH07100682B2 - Method for producing aminophenol alkyl ethers - Google Patents

Description

TECHNICAL FIELD OF THE INVENTION The present invention relates to a method for producing aminophenol alkyl ethers, and more specifically, to react aminophenols with a carbonic acid compound to selectively produce aminophenol alkyl ethers. It relates to a method that can be produced in high yield.

TECHNICAL BACKGROUND OF THE INVENTION AND PROBLEMS THEREOF Aminophenol alkyl ethers are useful substances as raw materials for manufacturing azo dyes, agricultural chemicals, naphthol paints and the like.

Conventionally, these aminophenol alkyl ethers have been produced by selectively alkylating the hydrogen atom of the hydroxyl group of aminophenols (0-alkylation reaction). And, in the 0-alkylation reaction of the aminophenol alkyl ethers, as an alkylating agent,
An alkylsulfate compound such as dimethylsulfate or an alkyl halide compound is used.

However, in the course of the 0-alkylation reaction using an alkylsulfate compound and an alkyl halide compound, the acid equivalent to the alkyl group is liberated, so the liberated acid must be neutralized. There has been a problem that the operation and the operation of removing the produced salt are very complicated.

Further, the alkylsulfate compound has a problem that it is difficult to handle because it is highly toxic.

Furthermore, it is necessary to form a reactor with a material that is corrosion resistant to the acid liberated by the reaction, the alkali used to neutralize it, and the salt produced by this neutralization reaction, and therefore There is also a facility problem that the materials that can be used for forming are very limited.

On the other hand, an alkyl carbonate compound is known as an alkylating agent for alkylating a hydroxyl group or an amino group substituted on a benzene ring. That is, for example, dimethyl carbonate and phenol can be reacted in the presence of a basic catalyst to give anisole, and aniline and dimethyl carbonate can be reacted in the presence of a basic catalyst to give N-
Methylamine or N, N'-dimethylamine can be obtained.

However, when attempting to alkylate an aminophenol having two functional groups, a hydroxyl group and an amino group, using a dialkyl carbonate compound such as dimethyl carbonate, the dialkyl carbonate compound is It is unknown which group it reacts with. Further, the conditions for producing aminophenol alkyl ethers by selectively advancing 0-alkyl compounds of aminophenols using dialkyl carbonate compounds have not been known at all.

OBJECT OF THE INVENTION The present invention is intended to solve the problems associated with the prior art as described above, and an object thereof is to provide a method capable of easily producing an aminophenol alkyl ether in a high yield. I am trying.

A further object of the present invention is to provide a method for producing aminophenol alkyl ethers which does not require complicated operations such as neutralization reaction and removal of neutralizing salts and which is less likely to corrode production equipment.

SUMMARY OF THE INVENTION The method for producing aminophenol alkyl ethers according to the present invention comprises: an aminophenol and a carbonic acid compound having two alkyl groups as a solvent, N, N-dimethylacetamide, N-methyl-2-
Pyrrolidone, hexamethylphosphoramide, tetramethylurea, a compound selected from the group consisting of sulfoxide compounds, 0.2 to 20 to the above aminophenols
Used in double weight, as catalyst, N, N-dimethylacetamide, N-methyl-2-
Pyrrolidone, hexamethylphosphoramide, tetramethylurea, a pyridine compound, a compound selected from the group consisting of tri-n-butylphosphine and triphenylphosphine, 1/500 times or more moles with respect to the aminophenols It is characterized in that it is used in an amount to react.

According to the method for producing aminophenol alkyl ethers of the present invention, aminophenols and a carbonic acid compound having two alkyl groups are reacted with a specific solvent and a catalyst to selectively give 0 -By advancing the alkylation reaction, aminophenol alkyl ethers can be produced with high yield and high selectivity.

Moreover, the 0-alkylating agent is a carbonic acid compound having two alkyl groups such as a dialkyl carbonate compound or a dialkyl carbonate compound, and since the acid is not liberated by the reaction, the reaction device is less likely to corrode and Since it is not released, the neutralization operation is unnecessary.

Further, these 0-alkylating agents have low toxicity and are extremely easy to handle as compared with the conventionally used alkylating agents.

DETAILED DESCRIPTION OF THE INVENTION The method for producing aminophenol alkyl ethers according to the present invention will be specifically described below.

Aminophenols In the present invention, aminophenols used as a starting material for producing aminophenol alkyl ethers can be represented by the following formula [I].

However, in the general formula [I], R ₁ represents a halogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group (preferably having a carbon number of 1 to 7), an alkoxy group, an ester group or a phenyl group. Moreover, n is 0-4.

Particularly in the present invention, it is preferable to use aminophenols in which n is 0.

Further, in the above formula [I], the amino group may be substituted at the ortho position, the meta position or the para position with respect to the hydroxyl group.

Specific examples of aminophenols that can be used in the present invention include o-aminophenol, m-aminophenol, p-aminophenol, 2-chloro-4-amino-phenol, and 2-chloro-6-amino. -Hydroquinone, 2-cyano-4-amino-phenol, p-nitro-resorcin, 4-
Amino-m-cresol and the like can be mentioned, and these can be used alone or in combination. Of these compounds, the particularly preferred compound is m-aminophenol.

Carbonic Acid Compound In the present invention, a carbonic acid compound having two alkyl groups is used as the 0-alkylating agent for the aminophenol.

The carbonic acid compound having two alkyl groups used in the present invention can be represented by the following formula [II].

In the above formula [II], P ₂ and R ₃ are each independently a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, specifically, a methyl group, an ethyl group, a propyl group and an isopropyl group. And the like, and the alkyl group having a substituent includes a benzyl group.

Therefore, as the carbonic acid compound having two alkyl groups used in the present invention, specifically, dimethyl carbonate,
Examples thereof include diethyl carbonate, di-n-propyl carbonate, diisopropyl carbonate, di-n-butyl carbonate, dibenzyl carbonate, methyl ethyl carbonate, methyl propyl carbonate, ethyl propyl carbonate and the like. These compounds can be used alone or in combination.

Among these carbonic acid compounds, preferred compounds are dimethyl carbonate, diethyl carbonate, di-n-propyl carbonate, methylethyl carbonate and dibenzyl carbonate, with dimethyl carbonate being particularly preferred.

Solvent In order to selectively carry out the 0-alkylation reaction by using a carbonic acid compound having two alkyl groups such as dimethyl carbonate as the aminophenols, either a tertiary amino compound or a sulfoxide compound can be used as a solvent. It is necessary to use one or both in combination.

The tertiary amino compound used as a solvent in the present invention is preferably a compound which is liquid at room temperature, and particularly has a melting point of 30.
It is preferable to use a tertiary amine compound having a temperature of 0 ° C. or higher.

Examples of such a tertiary amine compound include N, N-dimethylacetamide and N-methyl-2-pyrrolidone.

Further, examples of the sulfoxide compound include hexamethylphosphoramide and tetramethylurea.

In the present invention, the above compound alone as a solvent,
Alternatively, they can be used in combination.

In the present invention, as a solvent, among these, N, N-
By using dimethylacetamide, an A ratio {for example, [amount of m-anisidine produced / (amount of m-anisidine produced + N-
Methylanisidine production amount)] × 100} can be improved and the yield tends to be high, which is particularly preferable.

Catalyst In the present invention, one or both of a tertiary amine compound and a phosphine is used as a catalyst when reacting an aminophenol with a carbonic acid compound having two alkyl groups in the above specific solvent. Are used in combination.

That is, in the present invention, the catalyst comprises N, N-dimethylacetamide, N-methyl-2-pyrrolidone, hexamethylphosphoramide, tetramethylurea, a pyridine compound, tri-n-butylphosphine and triphenylphosphine. A compound selected from the group is used.

Of these, N, N-dimethylacetamide, N-methyl-
2-pyrrolidone, hexamethylphosphoramide, and tetramethylurea are the tertiary amine compounds shown above as solvents, and when these tertiary amine compounds are used,
This tertiary amine compound acts as a solvent and a catalyst.

In addition to these, it is also possible to use aniline compounds, chain-like tertiary amine compounds and other cyclic compounds, polymers having tertiary amino groups, and the like.

In the present invention, examples of the aniline compound that can be used as a catalyst include a compound in which a hydrogen atom bonded to a nitrogen atom of aniline is substituted with an alkyl group having 1 to 10 carbon atoms, and specifically, , Dimethylaniline, diethylaniline, di- (n-propyl) -aniline and dimethylethylamine.

Examples of the heterocyclic compound containing a nitrogen atom that can be used as a catalyst in the present invention include pyridine compounds, pyrazolidine compounds, imidazolidine compounds, morpholine compounds, piperidine compounds and pyrrolidine compounds. However, except the pyridine compound, the nitrogen atom constituting the heterocycle has a substituent having 1 to 10 carbon atoms.

Specific examples of the nitrogen-containing heterocyclic compound that can be used in the present invention include pyridine, 4-pyrrolidine- (1) -pyridine, o-methyl-pyridine, m-methyl-pyridine, o-ethyl- Pyridine, m-ethyl-pyridine, p-ethyl-pyridine, o-propyl-pyridine, m-propyl-pyridine, p-propyl-pyridine, p-methoxy-pyridine, p-ethoxy-pyridine, p-propoxy-pyridine, α-picoline, β-picoline, γ-picoline,
Quinoline, isoquinoline, quinazoline, quinoxaline,
N-methylimidazole, N-methylpyrrole, 2,6-lutidine, 2,4-lutidine, 2-dimethylaminopyridine, N, N-dimethylcyclohexylamine, pyrimidine, acridine, p-dimethylaminopyridine, p-diethylaminopyridine And p-dipropylaminopyridine and the like.

Examples of the chain tertiary amine compound that can be used as a catalyst in the present invention include trimethylamine, dimethylamino-neopentanol, N, N'-tetramethyldiamino-neopentane, ethyldimethylamine, lauryldimethylamine, stearyldimethylamine, Amyl dimethyl amine, propyl dimethyl amine, butyl dimethyl amine, etc. are mentioned.

Further, it can be used as a catalyst in the present invention.
Examples of polymers having a primary amino group include 4-polyvinyl pyridine and polyvinyl imidazole- (N).

In the present invention, as the phosphine compound as a catalyst,
Tri-n-butylphosphine or triphenylphosphine is preferable, and in addition to these, a compound represented by the following formula [III] or formula [IV] can also be used. The phosphine may be in the form of diphosphine.

In the above formulas [III] and [IV], R ₄ is an aliphatic hydrocarbon residue or an aromatic hydrocarbon residue. Specific examples of the aliphatic residue represented by R ₄ include an aliphatic hydrocarbon residue, preferably an alkyl group having 1 to 6 carbon atoms, and at least a hydrogen atom in the aliphatic hydrocarbon residue. An alkyl group having 2 to 9 carbon atoms substituted with one cyan group can be mentioned.

In addition, examples of the aromatic hydrocarbon residue represented by R ₄ include a substituted or unsubstituted phenyl group. Specific examples of the substituted phenyl group include a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms, a phenyl group substituted with an alkoxy group having a structural unit having 1 to 4 carbon atoms, and the above alkyl group or Examples thereof include a phenyl group having a substituent in which an alkoxy group is further substituted with a phenyl group. The formula [III] and the formula [I
V], R ₄ may be the same or different.

In the above formula [IV], R ₅ represents a divalent aliphatic hydrocarbon residue, preferably an alkylene group having 1 to 6 carbon atoms.
The alkylene groups are, for example, 1 to 4 respectively.
It may be substituted with a group inert to aminophenols and alkylating agents such as an alkyl group having 1 carbon atom, an alkoxy group or a carboalkoxy group having a structural unit having 2 to 4 carbon atoms.

That is, as the compound represented by the above formula [III] in the present invention, an alkylphosphine compound, a phenylphosphine compound, a tolylphosphine compound, a xylylphosphine compound, a phosphine compound having a polar group,
Other phosphine compounds may be mentioned. Examples of the compound represented by the formula [IV] include bis- (diphenylphosphino) -alkane.

Specific examples of the alkylphosphine compound that can be used as a catalyst in the present invention include trimethylphosphine, triethylphosphine, tripropylphosphine,
Triisopropylphosphine, tributylphosphine,
Triisobutylphosphine, tri-secondary butylphosphine, triphenylphosphine; P, P-dimethyl-P-neopentylphosphine, P-ethyl-P, P-dimethylphosphine, P-lauryl-P, P-dimethylphosphine, P -Stearyl-P, P-dimethylphosphine, P-amyl-P, P-dimethylphosphine, P-propyl-P, P-dimethylphosphine, P-
Butyl-P, P-dimethylphosphine, tri- (pentyl)
-Phosphine, tri- (n-hexyl) -phosphine, tri- (n-heptyl) -phosphine, tri- (n-octyl) -phosphine, tri- (n-nonyl) -phosphine,
Examples thereof include tri- (n-methyl) -phosphine.

As a concrete example of the phenylphosphine compound. P, p-
Examples thereof include dimethyl-P-phenylphosphine and tri- (2-methoxy) -phenylphosphine.

Specific examples of the tolylphosphine compound include tri-
(2-methoxy) -phenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine and the like can be mentioned.

Specific examples of the xylylphosphine compound include tri-o-xylylphosphine, tri-m-xylylphosphine, tri-p-xylylphosphine and the like.

Further, examples of the phosphine compound having a substituent include a phosphine compound having a substituent such as a cyano group or a carbonyl group, and specifically, P, P-bis- (2-cyaminoethyl) -P-phenyl Phosphine, tri- (2-cyanoethyl) -phosphine, tri- (carboethoxymethyl) -phosphine, P-carboethoxymethyl-P, P-diethylphosphine, P, P-diethyl-P- (β-
Carboethoxyethyl) -phosphine, P-carboethoxymethyl-P, P-diphenylphosphine and the like can be mentioned.

Further, specific examples of phosphine compounds other than the above, P-propyl-P-hexyl-P-nonyl-phosphine,
Examples include P-ethyl-P- (2-ethoxyethyl) -P-phenyl-phosphine, P-isopropyl-P, P-diphenyl-phosphine and P-butyl-P, P-diphenyl-phosphine.

Examples of the bis- (diphenylphosphino) -alkane represented by the above formula [IV] that can be used in the present invention include:
Examples thereof include compounds having an alkylene group having 1 to 6 carbon atoms, and specific examples include 1,2-bis- (diphenylphosphino) -ethane and bis- (ethylphenylphosphino) -alkane (for example, 1,2-bis- (ethylphenylphosphino) -ethane, 1,4-bis- (ethylphenylphosphino) -butane) bis- (dialkylphosphino) -alkanes (eg 1,5-bis- (diethylphosphine) Fino) -pentane) and the like.

These compounds can be used alone or in combination.

Reaction Conditions In the present invention, in the reaction of an aminophenol with a carbonic acid compound having two alkyl groups, a carbonic acid compound having two alkyl groups is used in an equivalent amount, an excess amount or an insufficient amount with respect to the aminophenols. Can be reacted.

Specifically, when a monohydroxy compound is used as the aminophenol and the corresponding monoether compound is obtained by 0-alkylation of the aminophenol, the carbonic acid having two alkyl groups is used for the aminophenol used. The compound is usually used in the range of 0.3 to 10-fold mol, preferably 0.8 to 5-fold mol. When a di- or trihydroxy compound is used as the aminophenol and the corresponding monoether compound is obtained by 0-alkylation, a carbonic acid compound having two alkyl groups is used for the aminophenol used. Usually, 0.1 to 5 times mol, preferably
It is used in the range of 0.2 to 2 times mol. Further, when a di- or trihydroxy compound is used as the aminophenol and the corresponding di- or triether compound is obtained by 0-alkylation of the compound, a carbonic acid compound having two alkyl groups for the aminophenol used. Is usually
It is used in an amount of 3 to 15 times mol, preferably 5 to 10 times mol.

The amount of the solvent used in the present invention can be appropriately set in consideration of the reaction conditions and the like, but particularly in the present invention, the amount of the solvent is 0.2 with respect to the aminophenols used.
It is desirable to use it in a weight of ˜20 times.

The amount of the catalyst used in the present invention is usually 1/500 times or more the molar amount of the aminophenols used.

In particular, in the present invention, when a tertiary amine compound is used as a solvent, the tertiary amine compound also acts as a catalyst, so that it is not necessary to add a catalyst separately. However, in this case, a tertiary amine compound other than the tertiary amine compound used as a solvent or a phosphine compound may be added in an optional addition amount.

In addition, when the tertiary amine compound and the sulfoxide compound are used in combination as the solvent, the amount of the tertiary amine compound used as the solvent is larger than that of the aminophenols.
If the molar ratio is 1/500 or more, it is not necessary to add a catalyst. However, in this case, a tertiary amine compound other than the tertiary amine compound used as a solvent or a phosphine compound may be added in an optional addition amount.

On the other hand, when a sulfoxide compound is used as the solvent, the catalyst is usually used in an amount of 1/500 times the molar amount of the aminophenols used as described above. Particularly, in this case, it is preferably used in the range of 1/500 to 1/20 times mole, and more preferably used in the range of 1/200 to 1/50 times mole.

Aminophenols and 2 using the above catalysts and solvents
The reaction with a carbonic acid compound having alkyl groups is usually
It can be carried out at a temperature of 100 to 300 ° C, preferably 120 to 230 ° C.

Further, this reaction can be carried out under normal pressure or under pressure, and particularly in the present invention, it is preferable to carry out the reaction under pressure.

Further, the reaction time is usually 0.5 to 10 hours, preferably 1 to 6 hours.

After the above reaction is completed, adjusting the pH value of the reaction solution within the range of 5 to 10 tends to improve the yield of aminoalkyl ether.

The reaction between the above aminophenols and the carbonic acid compound having two alkyl groups is represented by the following formula, for example.

In the above formula [V], R ₁ is a hydroxyl group, a halogen atom, a cyan group, a nitro group, an alkyl group, an alkoxyl group, an ester group or a phenyl group. Further, n = 0 to 4.

The aminophenol alkyl ethers obtained by the production method of the present invention as described above include p-anisidine, m-anisidine, p-isopropoxyphenyl ether, m-isopropoxyphenyl ether, pn propoxyphenyl ether, and m-butyl. Examples include foxyphenyl ether.

After the reaction is completed, the produced aminophenol alkyl ethers can be separated from the reaction solution by, for example, distilling the reaction mixture solution under reduced pressure.

EFFECTS OF THE INVENTION According to the present invention, when an aminophenol is reacted with a carbonic acid compound having two alkyl groups, a tertiary amine compound and / or a sulfoxide compound is used as a solvent, and a tertiary amine compound and a catalyst are used as a catalyst. By using the / or phosphine compound, the 0-alkylation reaction can be selectively proceeded to produce aminophenol alkyl ethers in high yield and high selectivity.

Moreover, the carbonic acid compound having two alkyl groups such as the dialkyl carbonate compound or the dialkyl carbonate compound used as the 0-alkylating agent does not liberate the acid in the reaction process, and effectively prevents the corrosion of the manufacturing apparatus. Moreover, since the acid is not liberated, the neutralization operation is unnecessary.

Also, these 0-alkylating agents have low toxicity and are very easy to handle.

The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

Example 1 m-aminophenol 2.7 was added to an autoclave having a volume of 100 ml.
3g (0.025mol), dimethyl carbonate 2.26g (0.025mol) and 45g of dimethylacetamide as solvent and catalyst
(0.52 mol) was charged. The ratio of each component charged in the autoclave is converted into a molar ratio, m-aminophenol; 1, dimethyl carbonate; 1, dimethylacetamide; 2
0.8.

Next, m-aminophenol and dimethyl carbonate were added at 180 ° C.
It was made to react at the temperature of 5 hours. The maximum internal pressure of the autoclave during the reaction was 3.5 kg / cm ² · G.

After the reaction was completed, a part of the reaction solution was taken out and analyzed by gas chromatography to find out the conversion rate of aminophenol, the yield of anisidine and the A ratio [amount of m-anisidine (mole) / (m-anisidine). Amount + N-methylanisidine amount)
× 100 was determined.

The results are shown in Table 1.

Then, 1.9 g of the reaction product was separated by vacuum distillation. The component ratio of the separated reaction product was measured by using gas chromatography, and the results are also shown in Table 1.

Example 2 In Example 1, the amount of dimethylacetamide used as a solvent was 6.3 g [0.073 mol, molar ratio; 2.92], and P-dimethylaminopyridine 15.3 was separately used as a catalyst.
mg [0.125 mmol, molar ratio; 0.005] used, reaction time;
The reaction was carried out for 3 hours under the conditions of a reaction temperature of 200 ° C. and a maximum reaction pressure of 11 kg / cm ² · G.

Table 1 shows the results obtained by measuring the conversion rate of aminophenol, the yield of anisidine, the A ratio, and the component ratio of the reaction product using gas chromatography, which were obtained in the same manner as in Example 1.

Example 3 In Example 1, the solvent and the amount of dimethylacetamide used as a catalyst were 32 g [0.37 mol, molar ratio; 1
4.7], the reaction time was 5 hours, the reaction temperature was 180 ° C., and the reaction maximum pressure was 3.0 kg / cm ² · G.

Table 1 shows the results obtained by measuring the conversion rate of aminophenol, the yield of anisidine, the A ratio, and the component ratio of the reaction product using gas chromatography, which were obtained in the same manner as in Example 1.

Example 4 A reaction was carried out in the same manner as in Example 3 except that the maximum reaction pressure was 3.2 kg / cm ² · G.

When the reaction was completed, the pH value of the reaction solution was measured and found to be 11.4.

Table 1 shows the results obtained by measuring the conversion rate of aminophenol, the yield of anisidine, the A ratio, and the component ratio of the reaction product using gas chromatography, which were obtained in the same manner as in Example 1.

Example 5 The same operation as in Example 4 was performed except that diluted phosphoric acid was added to the reaction solution after the reaction was completed to adjust the pH value to 5.4.

Table 1 shows the results obtained by measuring the conversion rate of aminophenol, the yield of anisidine, the A ratio, and the component ratio of the reaction product using gas chromatography, which were obtained in the same manner as in Example 1.

Example 6 In Example 1, triphenylphosphine 0.13 g, 0.5 mmol, molar ratio 0.02 was used as a catalyst, and dimethyl sulfoxide 28.5 g, 0.37 mol, molar ratio; 14.7.
The reaction was performed in the same manner except that was used.

Table 1 shows the results obtained by measuring the conversion rate of aminophenol, the yield of anisidine, the A ratio, and the component ratio of the reaction product using gas chromatography, which were obtained in the same manner as in Example 1.

Comparative Example 1 In Example 1, P-dimethylaminopyridine 79.5 was used as a catalyst without using dimethylacetamide as a solvent.
Using mg [0.65 mmol, molar ratio 0.026], reaction time; 3
The reaction was carried out under the conditions of time, reaction temperature: 200 ° C., maximum reaction pressure: 25 kg / cm ² · G.

Table 1 shows the results obtained by measuring the conversion rate of aminophenol, the yield of anisidine, the A ratio, and the component ratio of the reaction product using gas chromatography, which were obtained in the same manner as in Example 1.

Comparative Example 2 m-Aminophenol 2.73 g (0.25 mol) and dimethyl carbonate
4.5 g, 0.05 mol, [molar ratio to m-aminophenol; 1.2] as a catalyst, NaOH 2.0 g [0.05 mol, molar ratio to m-aminophenol; 1.2] and KI 0.083 g,
Using [0.5 mmol, the same molar ratio: 0.02] as a solvent,
The reaction was carried out using methanol at 150 ° C. for 3 hours, but anisidine was obtained only in a trace amount.

Comparative Example 3 In Example 1, 0.015 g of P-dimethylaminopyridine [0.12 milmol, molar ratio 0.005] was used as a catalyst, without using a solvent, reaction time: 3 hours, reaction temperature: 200 ° C., reaction maximum The reaction was carried out under the reaction conditions of pressure: 25 Kg / cm ² · G.

Table 1 shows the results obtained by measuring the conversion rate of aminophenol, the yield of anisidine, the A ratio, and the component ratio of the reaction product using gas chromatography, which were obtained in the same manner as in Example 1.

Claims (3)

[Claims] 1. An aminophenol and a carbonic acid compound having two alkyl groups as a solvent, N, N-dimethylacetamide, N-methyl-2-
A compound selected from the group consisting of pyrrolidone, hexamethylphosphoramide, tetramethylurea and sulfoxide compounds is added to the above aminophenols in an amount of 0.2
Used in an amount up to 20 times the weight of the catalyst, N, N-dimethylacetamide, N-methyl-2-
Pyrrolidone, hexamethylphosphoramide, tetramethylurea, a pyridine compound, a compound selected from the group consisting of tri-n-butylphosphine and triphenylphosphine, 1/500 times or more moles with respect to the aminophenols A method for producing an aminophenol alkyl ether compound, which comprises reacting the compound in a quantity. 2. An aminophenol compound represented by the following formula [I]: (However, in the formula [I], R ₁ represents a halogen atom, a hydroxyl group, a cyan group, a nitro group, an alkyl group, an alkoxy group, an ester group or a phenyl group, and n is 0 to 4) A carbonic acid compound which is a compound and has two alkyl groups has the following formula [II]; (In the formula [II], R ₂ and R ₃ each independently represent a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms) or a dialkyl carbonate compound or a dialkyl carbonate compound. The method for producing aminophenol alkyl ethers according to claim 1, wherein 3. The aminophenol alkyl according to claim 1, wherein the sulfoxide compound used as the solvent is a sulfoxide selected from the group consisting of dimethyl sulfoxide and diethyl sulfoxide. Method for producing ethers.