JPH11217376A - Production of alpha-alkenyl-2-oxazoline - Google Patents

Abstract

PROBLEM TO BE SOLVED: To make easily and industrially obtainable the subject compound in high operability and yield by dehydrocyclizing a specified feedstock compound in the presence of a basic substance to suppress byproduct tar due to the polymerization. SOLUTION: This compound of formula II is obtained by dehydrocyclization of a compound of formula I (R<1> is hydrogen or a 1-3C alkyl; R<2> , R<a> and R<b> are each hydrogen or methyl) in the presence of a basic substance (preferably a methoxide or a hydroxide of sodium or potasium) preferably at 200-250 deg.C and 100-200 mmHg. N-(2-hydroxyalkyl)-β-alkoxy substituted carboxylic acid amide, one of the compounds of formula I, is preferably obtained by reacting a (meth)acrylic ester of formula III (R<3> is a 1-3C alkyl) with lower alcohol of the formula R<1> -OH (R<1> is a 1-3C alkyl) on the presence of a basic catalyst and the resultant β-alkoxy substituted carboxylic acid ester is reacted with a β-aminoalkanol.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a compound represented by the general formula (I):

[0002]

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Wherein R ² , R ^a , and R ^b each independently represent a hydrogen atom or a methyl group, and a method for producing α-alkenyl-2-oxazoline. The α-alkenyl-2-oxazoline provided by the present invention is a “bifunctional monomer” generally referred to in the art, and has two different reactive groups in the same molecule. For example, a carbon-carbon double bond can be polymerized with a known radical initiator or elevated temperature to form a copolymer with polyalkenyl oxazoline or another radically polymerizable monomer. The oxazoline ring can be reacted with a compound having active hydrogen such as carboxylic acid, or hydrolyzed with an alkali, and quaternized with methyl iodide.

Accordingly, the α-alkenyl-2-oxazoline provided by the present invention can be used as a raw material for various reactive polymers, polymer cross-linking agents, ion exchange resins, organic synthesis, etc. by utilizing these characteristics. Is a useful monomer that can be frequently used as

[0005]

2. Description of the Related Art Heretofore, several methods for producing .alpha.-alkenyl-2-oxazoline have been proposed. For example, Japanese Unexamined Patent Publication (Kokai) No. 3-502797 discloses an aminolysis of methacrylic acid ester and β-aminoalkanol in the presence of a base catalyst such as sodium methylate to synthesize N- (2-hydroxyalkyl) -methylacrylamide. And
There is described a method of synthesizing α-isopropenyl-2-oxazoline by reacting the resulting product in a high-temperature medium in the presence of a weak Lewis acid catalyst. This method produces α-alkenyl-2-oxazoline by a simplified process without protecting a highly reactive carbon-carbon double bond, and is apparently excellent. However, this reaction method has a yield of about 70% or more, which is not satisfactory. In addition, in the actual operation, since the reaction is carried out without protecting a highly active carbon-carbon double bond, various side reactions occur, and in particular, a large amount of tar is generated by polymerization in the cyclization dehydration step, and , Derived from a difunctional monomer,
There is a disadvantage that a crosslinking reaction or the like occurs, and the viscosity of the reaction mixture increases with the lapse of the reaction time, making it difficult to stably operate. In addition, after the reaction is completed, with respect to the withdrawal operation of the reaction vessel liquid, because of its high viscosity, it is necessary to withdraw at a high temperature or to add a solvent or the like in order to lower the viscosity. Is not preferred.

Japanese Patent Publication No. 54-4954 discloses α, β.
-After the addition of an alcohol to the unsaturated nitrile to protect the active olefin, a β-alkoxy-2-oxazoline is formed by reaction with a β-aminoalkanol in the presence of a catalyst, which is further removed in the next step. A method for producing an α-unsaturated-2-oxazoline by regenerating an olefin has been proposed. This method is an improvement over the above-described reaction in that an attempt is made to protect the active olefin to suppress side reactions such as polymerization, but it was used as a protecting group in the step of performing a cyclization reaction to oxazoline. There is a disadvantage that the alcohol is eliminated and the polymer is increased as a result.

JP-B-58-4028 discloses that cyclobutane-1,2-dinitrile is reacted with β-aminoalkanol in the presence of a catalyst to form bis-oxazoline, which is then thermally cleaved to give α-vinyl. A method for producing -2-oxazoline has been proposed. In this method, polymerization does not occur at the time of oxazoline formation as in the above example, but on the contrary, since it is thermally stable, it is 400 ° C. for cleavage.
The above high temperature is required, and the operation becomes complicated such as reaction in the gas phase. Also, it is difficult to obtain dinitrile as a raw material.

[0008] In addition to the above examples, there are known methods for producing α-alkenyl-2-oxazoline, but none of these methods is satisfactory from an industrial point of view.

[0009]

Accordingly, an object of the present invention is to provide a method for industrially producing α-alkenyl-2-oxazoline easily, with good operability and with high yield. is there.

[0010]

DISCLOSURE OF THE INVENTION The present inventors have suppressed the by-product of tar by polymerization, and have obtained α-alkenyl-2 in good yield.
As a result of intensive studies on the method for producing oxazoline, general formula (II)

[0011]

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(Wherein R ¹ is a hydrogen atom or a group having 1 to 1 carbon atoms)
And R ² , R ^a , and R ^b represent the general formula (I)
Are the same as those in the above), and a method for producing the desired α-alkenyl-2-oxazoline in high yield by a one-step reaction of dehydrating and cyclizing the compound represented by the formula Thus, the present invention has been completed.

That is, the present invention provides a compound represented by the general formula (I):

[0014]

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(Wherein R ² , R ^a and R ^b each independently represent a hydrogen atom or a methyl group), in the method for producing α-alkenyl-2-oxazoline represented by the general formula (II):

[0016]

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(Wherein R ¹ is a hydrogen atom or a group having 1 to 1 carbon atoms)
And R ² , R ^a , and R ^b represent the general formula (I)
Wherein the compound represented by the formula (1) is dehydrated and cyclized in the presence of a basic substance, and a process for producing α-alkenyl-2-oxazoline is provided. Also,
In the above, it is provided that the basic substance is at least one selected from the group consisting of oxides, hydroxides and alkoxides of alkali metals and / or alkaline earth metals.

In the above, the compound represented by the general formula (II)
Is a compound represented by the general formula (II) ¹Has 1 to 3 carbon atoms
N- (2-hydroxyalkyl) -β which is an alkyl group
An alkoxy-substituted carboxylic acid amide, wherein the N- (2
-Hydroxyalkyl) -β-alkoxy-substituted carboxyl
The acid amide has the general formula (III)

[0019]

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(Wherein, R ² is the same as that in the general formula (I), and R ³ represents an alkyl group having 1 to ³ carbon atoms). General formula (I
V)

[0021]

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(Wherein R ¹ is an alkyl group having 1 to 3 carbon atoms) and reacted in the presence of a base catalyst to obtain a compound represented by the general formula (V):

[0023]

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[0024] (In the formula, R ¹ is an alkyl group having 1 to 3 carbon atoms, R ² is the same as in the general formula (I), R ³
Is the same as that in formula (III)).
Synthesizing an alkoxy-substituted carboxylic acid ester,
A product obtained by reacting β-aminoalkanol therewith is provided.

[0025]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.
R ^{1 of the} compound represented by the general formula (II) used in the present invention
Represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms;
² represents a hydrogen atom or a methyl group. In addition, the general formula (I
Specific examples of the compound represented by I) include N- (2
-Hydroxyethyl) -β-hydroxypropionic acid amide; N- (2-hydroxyethyl) -β-hydroxyisobutyric acid amide; N- (2-hydroxyethyl) -β-
Methoxypropionamide, N- (2-hydroxyethyl) -β-ethoxypropionamide, N- (2-
N- (2-hydroxyalkyl) -β-alkoxy-substituted propionamides such as (hydroxyethyl) -β-n-propoxypropionamide, N- (2-hydroxyethyl) -β-isopropoxypropionamide;
-(2-hydroxyethyl) -β-methoxyisobutyric acid amide, N- (2-hydroxyethyl) -β-ethoxyisobutyric acid amide, N- (2-hydroxyethyl) -β-n
N- such as propoxyisobutyric amide and N- (2-hydroxyethyl) -β-isopropoxyisobutyric amide;
(2-hydroxyalkyl) -β-alkoxy-substituted isobutyric acid amide and the like can be mentioned.

Among the compounds represented by the general formula (II) used in the present invention, N- (2-hydroxyalkyl) -β-
Alkoxy-substituted carboxylic acid amide (R ^{1 of the} general formula (II)
Is an alkyl group having 1 to 3 carbon atoms), these compounds are represented by the general formula (IV) in the presence of a base catalyst in a (meth) acrylic ester represented by the general formula (III) A β-alkoxy-substituted carboxylic acid ester represented by the general formula (V) is synthesized by adding a lower alcohol represented by the formula (V), and then reacted with a β-aminoalkanol to easily obtain the β-alkoxy-substituted carboxylic acid ester. These manufacturing methods will be described later.

In the present invention, a cyclodehydration catalyst can be used for dehydration cyclization of the compound represented by the general formula (II). As the dehydration cyclization catalyst, N- (2
Any catalyst capable of converting (-hydroxyethyl) carboxylic amide to 2-oxazoline can be used without limitation.

[0028]

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(Wherein R represents a hydrocarbon residue) The cyclization reaction of N- (2-hydroxyethyl) carboxylic amide exemplified by the formula A is generally carried out in a liquid phase of a high-temperature medium. With a weak Lewis acid. The cyclization reaction is a known reaction for producing 2-oxazoline, and is described, for example, in U.S. Pat. No. 3,681,333 to Litt et al. (1972).
It is described in documents such as U.S. Pat. No. 4,354,029 to Kaiser (1982) and U.S. Pat. No. 3,312,714 to Eisen Brown (1967). Among these, among the known dehydration cyclization catalysts, the reaction of the formula A is predominantly carried out under the reaction conditions of a reaction temperature of 150 to 300 ° C., and N- (2-hydroxyethyl) carboxylic acid amide is converted to 2-oxazoline. Any metal-containing compound having an ability to convert to a metal can be used in the present invention without limitation.

Specific examples of the dehydration cyclization catalyst used in the present invention include oxides, hydroxides, halides, sulfates, and organic carboxylate salts of zinc metal and / or iron metal. Can be. More specifically, for example, zinc oxide, zinc hydroxide, zinc chloride, zinc sulfate, zinc acetate, zinc formate, zinc propionate, zinc stearate, zinc decanoate, ferric chloride, ferric sulfate and the like Can be mentioned. More preferred catalysts are zinc oxide, zinc acetate, zinc chloride, ferric chloride and the like.

The basic substance used coexisting during the dehydration cyclization can be used without any particular limitation as long as it is stable under the reaction conditions and can be dissolved in the reaction mixture. And / or of alkaline earth metals,
Oxides, hydroxides, alkoxides and the like can be exemplified. The basic substance is more preferably an alkali metal hydroxide or lower alkoxide, and further preferably an alkali metal methoxide or hydroxide.
The alkali metal is preferably lithium, sodium or potassium, more preferably sodium or potassium.

Although the action of the basic substance is not clearly understood, the substituent R ^{1 at} the β-position of the compound represented by the general formula (II)
O- acts to regenerate desorbed olefin under the reaction conditions as water or a lower alcohol, after the compound represented by the general formula (II) by dehydration cyclization to oxazolines of, as described above, R ¹ O -Acts as a water or lower alcohol to remove under the reaction conditions to regenerate the olefin, or a dehydration cyclization catalyst and a basic substance cooperate to form an R ¹ O- group as water or a lower alcohol. It is conceivable that the elimination reaction and the cyclization reaction occur at the same time to act to produce α-alkenyl-2-oxazoline. Although the method of action cannot be specified, the presence of a basic substance under the reaction conditions at the time of the dehydration cyclization allows the compound represented by the general formula (II) to be obtained in one step at a high yield from the compound represented by the general formula (II). Α-Alkenyl-2-oxazoline represented by I) can be synthesized. This is a feature disclosed for the first time by the present invention.

The reaction in the present invention is inert to the reactants under the reaction conditions, is capable of dissolving the compound represented by the general formula (II) and the basic substance, and It is preferable to carry out the reaction in a solvent capable of maintaining a liquid and stable state. As long as the solvent satisfies the above requirements, it can be used without particular limitation. Specific examples of such a solvent include, for example, several kinds of glycol ethers, several kinds of polyglycol glycerol, sulfolane and the like. be able to.

The reaction temperature must, of course, be sufficient for the olefin regeneration reaction and the dehydration cyclization reaction to take place simultaneously and rapidly, and usually from about 180 to about 3
It is selected in the range of 00 ° C. The preferred reaction temperature is about 20
It has been found in the temperature range of 0 to about 250 ° C. The reaction pressure is such that the compound represented by the general formula (II) maintains a liquid state at the reaction temperature, and water or a lower alcohol derived from the R ¹ O-substituent of the compound represented by the general formula (II) It is preferable that the pressure be in a pressure range such that when α-alkenyl-2-oxazoline is further formed from water accompanying the oxazolination and further, α-alkenyl-2-oxazoline is promptly distilled off from the reaction system. Therefore, this reaction is preferably performed under reduced pressure. The pressure range is preferably 50 to 400 mmHg,
More preferably, it is 100 to 200 mmHg. If α-alkenyl-2-oxazoline is not distilled off promptly, α-alkenyl-2-oxazoline will be exposed to high temperatures and catalysts for a long time, polymerizing between the double bonds, or Rings may undergo ring-opening polymerization.

The production method of the present invention can be carried out by a batch method or a continuous method, but is preferably carried out by a continuous method in order to suppress the polymerization reaction. As an embodiment of the continuous method, for example, a reactor equipped with a distillation column, using the above-mentioned inert solvent, to a reaction mixture in which a dehydration cyclization catalyst and a basic substance coexist, to the above-mentioned reaction temperature and reaction pressure Under the adjusted reaction conditions, the compound represented by the general formula (II) is continuously or intermittently fed, and the produced α-alkenyl-2-oxazoline is mixed with water and the compound represented by the general formula (II). The water or lower alcohol derived from the R ¹ O-substituent is distilled off. The feed rate of the compound of general formula (II) is metered into the reactor at essentially the same rate as the amount of product distilled off.

The amount of the dehydration cyclization catalyst used in the present invention is usually 0.005 to 0.4 mol per 1 mol of the compound represented by the general formula (II). More or less can be used if desired. The amount of the basic substance used in the present invention is usually 0.01 to 0.2 per mole of the compound represented by the general formula (II).
It is used in molar amounts, but can be used more or less if necessary.

In carrying out the reaction according to the present invention,
It is preferable to add a known polymerization inhibitor for the purpose of suppressing polymerization. Phenothiazine is effective for this purpose. The α-alkenyl-2-oxazoline, water and lower alcohol distilled out from the above dehydration cyclization reaction and olefin group regeneration reaction are condensed by a known method. Recovery of α-alkenyl-2-oxazoline from condensed liquid
Separation can be performed by a known method such as extraction or distillation.

Next, the general formula (I) used in the present invention
Of the compounds represented by I), N- (2-hydroxyalkyl) -β- wherein R ¹ is an alkyl group having 1 to 3 carbon atoms.
A method for producing an alkoxy-substituted carboxylic acid ester will be described. The N- (2-hydroxyalkyl) -β-alkoxy-substituted carboxylic acid ester is obtained by adding the (meth) acrylic acid ester represented by the general formula (III) to the above-mentioned general formula (IV) in the presence of a base catalyst. The lower alcohol is added to synthesize a β-alkoxy-substituted carboxylic acid ester represented by the general formula (V), which is then easily reacted with a β-amino alcohol.

This method is based on the above-mentioned α-alkenyl-2.
-Prior to the production of oxazoline, it can be carried out as a series of steps to produce a raw material. The N- (2-
A process for preparing a (hydroxyalkyl) -β-alkoxy-substituted carboxylic acid amide as a previous step and then preparing an α-alkenyl-2-oxazoline is a feature disclosed by the present invention.

The (meth) acrylates represented by the general formula (III) used in the present invention include methyl acrylate, ethyl acrylate, n-propyl acrylate,
Examples include isopropyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, and isopropyl methacrylate. The lower alcohol represented by the general formula (IV) to be reacted with these is
Examples include methanol, ethanol, n-propanol, and isopropanol.

[0041] R ¹ of the compound represented by the general formula (V) used in the present invention, when R ^2, the R ³ specifically exemplified, R ¹ is
R ² is a hydrogen atom or a methyl group; R ³ is a methyl group, an ethyl group, an n-propyl group, or an isopropyl group. Further specific examples of the compound represented by the general formula (V) include: methyl ester, ethyl ester, n-propyl ester and isopropyl ester of β-methoxypropionic acid; methyl ester and ethyl ester of β-ethoxypropionic acid. Ester, n-propyl ester, isopropyl ester; β-n-propoxypropionic acid, methyl ester, ethyl ester, n-propyl ester, isopropyl ester; β-isopropoxypropionic acid, methyl ester, ethyl ester, n-
Propyl ester, isopropyl ester; β-methoxyisobutyric acid, methyl ester, ethyl ester, n-
Propyl ester, isopropyl ester; β-ethoxyisobutyric acid, methyl ester, ethyl ester, n-
Propyl ester, isopropyl ester; methyl ester, ethyl ester, n-propyl ester, isopropyl ester of β-n-propoxyisobutyric acid;
And methyl ester, ethyl ester, n-propyl ester, and isopropyl ester of isopropoxyisobutyric acid.

The molar ratio of the lower alcohol to the (meth) acrylic acid ester is preferably 0.5 to 1
0, more preferably 1 to 5. The reaction temperature of the reaction between (meth) acrylates and lower alcohols is 50
~ 130 ° C is preferred. As the catalyst for adding the lower alcohol to the (meth) acrylates, a basic catalyst is preferred, and examples thereof include sodium methylate, potassium hydroxide, and sodium hydroxide.

Next, β represented by the obtained general formula (V)
N- (2-hydroxyalkyl) -β-alkoxy-substituted carboxylic acid amide can be synthesized by aminolysis of -alkoxy-substituted carboxylic acid ester and β-aminoalkanol. Specific examples of the β-aminoalkanol used in the present invention include 2-aminoethanol, 2-amino-1-propanol, and 1-amino-2-.
Examples thereof include propanol, 3-amino-2-propanol, and 3-amino-2-butanol.

The molar ratio of β-aminoalkanol to β-alkoxy-substituted carboxylic acid ester is preferably in the range of 0.5 to 3, more preferably 1 to 1.5. The reaction between the β-alkoxy-substituted carboxylic acid ester and the β-aminoalkanol may be carried out in a lump at a time, or the reaction may be carried out while adding the other to either one, if used within the above-mentioned usage range. Is also good.

The reaction temperature of the reaction between the β-alkoxy-substituted carboxylic acid ester and the β-aminoalkanol is 30 to
150 ° C. is preferred. In the aminolysis, alcohol produced as a by-product may be distilled off after completion of the reaction, or the reaction may be carried out while distilling off from the reaction system. The latter is more advantageous in increasing the reaction rate and the conversion.

The reaction of the β-alkoxy-substituted carboxylic acid ester with the β-aminoalkanol proceeds without a catalyst because β-aminoalkanol is basic.
It is also possible to add a known basic aminolysis catalyst. The resulting N- (2-hydroxyalkyl) -β
The alkoxy-substituted carboxylic acid amide may be purified by vacuum distillation and used in the next step, but after the reaction is completed, only undistilled raw materials and low-boiling by-products are distilled off and used in the next reaction. Is also possible.

[0047]

EXAMPLES The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to the following examples. <Example 1> In a 300 ml reactor equipped with a stirrer, a thermometer, a measuring pump, and a top take-out 10-stage distillation column, 100 g of sulfolane as a solvent, 13.4 g of zinc oxide as a dehydration cyclization catalyst, and NaOMe (sodium) as a basic substance were used. 6.0 g of methylate) and 2.0 g of phenothiazine as a polymerization inhibitor were charged. The reaction was performed while adjusting the reaction pressure to 150 mmHg and the reaction temperature to 220 to 225 ° C. N-
Feeding 600 g of (2-hydroxyethyl) -β-hydroxypropionamide at a rate of about 1.67 g / min;
A distillate mainly composed of water and α-vinyl-2-oxazoline was recovered from the upper part of the distillation apparatus.

After the end of the supply of N- (2-hydroxyethyl) -β-hydroxypropionamide, the reaction temperature was raised by about 10 ° C., and the distillate was recovered for about 30 minutes.
Together with the distillate, it was analyzed by gas chromatography. As a result, 296.8 g of α-vinyl-2-oxazoline was contained in the distillate. This corresponds to a yield of 75% based on the feedstock. <Examples 2 to 5> Using the same apparatus as in Example 1, the conditions were changed to those shown in Table 1, and the same operation was performed.

[0049]

[Table 1]

Example 6 [Addition of alcohol] In an eggplant type flask equipped with a reflux condenser,
400.4 g (4 mol) of methyl methacrylate, 320.4 g (10 mol) of methanol, NaOMe as a catalyst
(Sodium methylate) 12 g was added and the temperature was 34 ° C.
And reacted for 4 hours. After completion of the reaction, an equivalent amount of acetic acid was added to neutralize the catalyst. The low-boiling substances were removed under reduced pressure and heating to obtain 480.6 g of methyl β-methoxyisobutyrate.

[Aminolysis] In a round bottom flask equipped with a stirrer, 240 g of ethanolamine, 6.4 g of sodium methoxide and 2.0 g of phenothiazine were added, and the mixture was heated at 40 ° C.
The methyl-β-methoxyisobutyrate 460 obtained by the above-mentioned alcohol addition reaction was taken for 2 hours while maintaining the following temperature.
g was added dropwise. After the completion of the dropwise addition, the reaction was continued for 1 hour.

After the completion of the reaction, the mixture was heated so as to maintain the temperature at about 40 to about 45 ° C., the pressure was gradually reduced, and a vacuum pump was applied to a final pressure of 10 mmHg to distill off light boiling substances such as methanol produced by aminolysis. The residue was 586 g, of which 558 g of N- (2-hydroxyethyl) -β-methoxyisobutyric acid was contained.

[Dehydration cyclization reaction] Using the same apparatus as in Example 1, 100 g of sulfolane as a solvent, 13.4 g of zinc oxide as a dehydration cyclization catalyst, and NaOMe as a basic substance
6.0 g of (sodium methylate) and 2.0 g of phenothiazine as a polymerization inhibitor were added, and the same operation as in Example 1 was performed. In addition, 550 g of the crude N- (2-hydroxyethyl) -β-methoxyisobutyric acid obtained in the [aminolysis] step was supplied at a rate of about 1.75 g / min, and water, methanol and α were fed from the upper part of the distillation apparatus. A distillate containing isopropenyl-2-oxazoline as a main component was recovered. After the feed of the raw materials was completed, the reaction temperature was increased by about 15 ° C., and the distillate was collected for about 30 minutes, and analyzed by gas chromatography together with the distillate, which revealed that α-isopropenyl-2-oxazoline was obtained. Was formed in an amount of 76 mol% based on methyl methacrylate. However, in the above calculation, methyl methacrylate which was not reacted and recovered in the alcohol addition reaction was excluded. The recovered methyl methacrylate and methanol can be used in the next reaction.

[0054]

According to the present invention, α-alkenyl-2-
Oxazoline can be industrially produced easily, with good operability and with high yield.

Claims (3)

[Claims] 1. A compound of the general formula (I) (Wherein, R ² , R ^a , and R ^b each independently represent a hydrogen atom or a methyl group).
In a process for producing oxazoline, a compound represented by the general formula (II): (Wherein, R ¹ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R ² , R ^a , and R ^b are the same as those in formula (I)). A process for producing α-alkenyl-2-oxazoline, comprising dehydration cyclization in the presence of a basic substance. 2. The α-alkenyl-2 according to claim 1, wherein the basic substance is at least one selected from the group consisting of oxides, hydroxides and alkoxides of alkali metals and / or alkaline earth metals. -A process for producing oxazolines. 3. A compound represented by the general formula (II), wherein R ¹ in the general formula (II) is an alkyl group having 1 to 3 carbon atoms.
-(2-hydroxyalkyl) -β-alkoxy-substituted carboxylic acid amide, wherein the N- (2-hydroxyalkyl) -β-alkoxy-substituted carboxylic acid amide has a general formula
(III) (Wherein, R ² is the same as in the general formula (I), R ³
Represents an alkyl group having 1 to 3 carbon atoms) and a (meth) acrylate represented by the general formula (IV): (Wherein R ¹ is an alkyl group having 1 to 3 carbon atoms) is reacted in the presence of a base catalyst to obtain a compound represented by the general formula (V): (Wherein, R ¹ is an alkyl group having 1 to 3 carbon atoms, R ² is the same as that in the general formula (I), and R ³ is a general formula (III)
Wherein the β-alkoxy-substituted carboxylic acid ester represented by the formula (1) is synthesized and then reacted with a β-aminoalkanol. A method for producing the described α-alkenyl-2-oxazoline.