JPH07126204A - Production of alkenyl phenyl ethers - Google Patents

Abstract

PURPOSE:To provide a process for producing an alkenyl phenyl ether from a phenolic compound and an alkenyl halide in high yield. CONSTITUTION:An alkenyl phenyl ether can be produced by reacting a phenolic compound with an alkenyl halide in a mixture of water and a ketone in the presence of a phase-transfer catalyst and an alkali.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing alkenyl phenyl ethers in high yield. The alkenyl phenyl ethers obtained by the present invention are organic synthetic intermediates of various fine chemicals,
It is a compound useful as a raw material for polymer production, a polymer modifier, and the like.

[0002]

2. Description of the Related Art Reactions for synthesizing alkenyl phenyl ethers by reacting phenols with alkenyl halides in the presence of alkali are known [eg Organic Reactions, 2 , 26, etc.] The yield is low when the compounds and the alkenyl halide are reacted simply in the presence of an alkali, and unreacted phenols remain in the reaction system, and a purification step such as distillation or alkali extraction is required after the reaction is completed. Therefore, it is disadvantageous as an industrial method for inexpensively producing the target product. Further, when reacting phenols and alkenyl halides, using dichloromethane as a reaction solvent, a method of synthesizing alkenyl phenyl ethers in the presence of a phase transfer catalyst is known (for example, tetrahedron, vol. ． 30, 13
79), this method also has a problem that the yield of alkenylphenyl ethers is low (about 50% of the theoretical amount).

[0003]

The present invention provides a method for producing alkenyl phenyl ethers in high yield from phenols and alkenyl halides.

[0004]

Means for Solving the Problems As a result of various investigations for achieving the above object, the present inventors have found that when phenols and alkenyl halides are reacted in the presence of an alkali to produce alkenyl phenyl ethers, It was found that by using a water-ketone mixed solvent as a reaction solvent and reacting in the presence of a phase transfer catalyst, unreacted phenols do not remain and alkenyl phenyl ethers can be obtained in high yield. Has been completed. That is, the present invention relates to a method for producing alkenyl phenyl ethers, which comprises reacting a phenol with an alkenyl halide in a water-ketone mixed solvent in the presence of a phase transfer catalyst and an alkali.

The present invention will be described in detail below. Phenols The phenols used in the present invention are not particularly limited as long as they are compounds having a phenolic hydroxyl group, and for example, a monovalent phenol represented by the following general formula [1], the following general formula [2] or [3] ] The dihydric phenol and trihydric or more polyhydric phenol shown by these can be used.

[0006]

[Chemical 1]

[Wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵
Are each independently a hydrogen atom, a halogen atom, an alkyl group,
Indicates an alkoxy group, nitro group, amino group, alkenyl group, phenyl group or substituted phenyl group]

[0008]

[Chemical 2]

[Wherein R ⁶ , R ⁷ , R ⁸ and R ⁹ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a nitro group, an amino group, an alkenyl group, a phenyl group or a substituted phenyl group. Show]

[0010]

[Chemical 3]

[Wherein R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a nitro group, an amino group, an alkenyl group, a phenyl group or a substituted phenyl group. , M is 0 or 1, and X is S, SO ₂ , O,

[0012]

[Chemical 4]

Or

[0014]

[Chemical 5]

And R ¹⁴ and R ¹⁵ are a hydrogen atom, an alkyl group, a phenyl group, a substituted phenyl group, a trifluoromethyl group or a trichloromethyl group, which may be the same or different.

Preferable specific examples of the monovalent phenol represented by the general formula [1] include phenol, o-cresol, m-cresol, p-cresol, 4-ethylphenol, 2-ethylphenol, 6-ethylphenol. , 4-propylphenol, 4-n-butylphenol, 4-tert-butylphenol, 2,4-dimethylphenol, 2,6-dimethylphenol, 2-chlorophenol, 4-chlorophenol, 6-chlorophenol, 4-bromo Phenol, 4-fluorophenol, 4-methoxyphenol, 2-methoxyphenol, 4-ethoxyphenol, 4-propyloxyphenol, 4-amyloxyphenol, 4-nitrophenol, 3-nitrophenol, 2-nitrophenol, 4 -Aminopheno , 3-amino-phenol, 2
-Allylphenol, 4-allylphenol, 2,4-
Diallylphenol, 2-methallylphenol, 4-methallylphenol, 2,4-dimethallylphenol, 2
-Phenylphenol, 3-phenylphenol and 4
-Phenylphenol, etc.

Preferred specific examples of the divalent phenol represented by the general formula [2] include o-dihydroxybenzene, m-dihydroxybenzene, p-dihydroxybenzene, 2,4-dihydroxy-1-chlorobenzene,
1,4-dihydroxy-2-chlorobenzene, 3,4-
Dihydroxy-1-chlorobenzene, 1,2-dihydroxy-4-methylbenzene, 1,3-dihydroxy-5
-Methylbenzene, 3,4-dihydroxy-1-methylbenzene, 1,2-dihydroxy-3-methoxybenzene, 1,4-dihydroxy-2-methoxybenzene,
1,4-dihydroxy-2-nitrobenzene, 3,4-
Examples include dihydroxy-1-aminobenzene and 1,3-dihydroxy-5-phenylbenzene.

Preferred specific examples of the divalent phenol represented by the general formula [3] are 2,2-bis [4-hydroxy-phenyl] propane and 2,2-bis [4-hydroxy-5-methyl-]. Phenyl] propane, 2,2-bis [4-hydroxy-3-methoxy-phenyl] propane, 2,2-bis [4-hydroxy-3-chloro-phenyl] propane, 3,3-bis [4-hydroxy- Phenyl] pentane, 1,1,1,3,3,3-hexafluoro-2,2-bis [4-hydroxy-phenyl] propane, 1,1,1,3,3,3-hexachloro-2,2
-Bis [4-hydroxy-phenyl] propane, bis [4-hydroxy-phenyl] methane, 1,1-bis [4-hydroxy-phenyl] ethane, 4,4'-dihydroxy-biphenyl, bis [4-hydroxy- Phenyl] thioether, bis [4-hydroxy-phenyl]
Ether, bis [4-hydroxy-phenyl] sulfone, 2,2-bis [3-hydroxy-phenyl] propane and the like. Specific examples of trihydric or higher polyhydric phenols include 2,2-bis [3,5-dihydroxy-phenyl] propane and 4- {4- [1,1-bis (4-hydroxyphenyl) ethyl]. Examples include -α, α-dimethylbenzyl} phenol, 1,1,1-tris (4-hydroxyphenyl) ethane, and cresol-type or novolac-type phenolic resins.

Alkenyl Halide The alkenyl halide in the present invention has 2 to 1 carbon atoms.
Those having 0 alkenyl group are preferable, and specific examples thereof include allyl chloride, allyl bromide, allyl iodide, methallyl chloride, methallyl bromide,
Examples thereof include methallyl iodide, crotyl chloride, crotyl bromide, vinyl chloride and vinyl bromide.

Alkali Further, the alkali in the present invention is preferably one that is soluble in a polar solvent, such as an organic compound or an inorganic compound. Specific examples of organic compounds include aliphatic amines such as ethylamine, diethylamine and triethylamine; aromatic amines such as aniline and dimethylaniline; cyclic organic bases such as pyridine, quinoline and piperidine; hydrazine derivatives such as phenylhydrazine; Ammonium; sulfonium base, etc .; specific examples of inorganic compounds include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide; alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide. Alkali metal carbonates such as sodium carbonate and potassium carbonate; and alkaline earth metal carbonates such as magnesium carbonate and calcium carbonate. If desired, two or more kinds of the above alkalis may be used in combination. When the alkali is added to the reaction system, the alkali may be a solid or a solution such as an aqueous solution.

Reaction solvent Since the reaction raw materials such as phenols and alkalis used in the present invention have poor compatibility, the reaction proceeds smoothly,
It is necessary to use a water-ketone mixed solvent in order to obtain the desired product in high yield. The ketone in the present invention is not particularly limited as long as it can be used as a reaction solvent, and specific examples include the following compounds. That is, acetone, diethyl ketone, methyl ethyl ketone, methyl isobutyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone,
Methyl-n-hexyl ketone, ethyl-n-butyl ketone, di-n-propyl ketone, diisobutyl ketone, mesityl oxide, phorone, isophorone, cyclohexanone, methylcyclohexanone, acetonylacetone, diacetone alcohol, acetophenone and diphenone. . Among the above ketones, the compound represented by the following general formula [4] is a preferred ketone in the present invention. R ¹⁶ CO (YCO) _n R ¹⁷ [4] (In the above formula, both R ¹⁶ and R ¹⁷ have 1 carbon atoms.
A 6 saturated or unsaturated hydrocarbon, R ¹⁶ and R ¹⁷ are
A ring may be formed by a carbon-carbon bond, Y is a hydrocarbon having 1 to 3 carbon atoms, and n is 0 or 1. ) Among the ketones represented by the above general formula [4], a compound in which R ¹⁶ and R ¹⁷ are saturated or unsaturated hydrocarbons having 1 to 4 carbon atoms is a more preferable compound, and the reaction is completed in a short time. Particularly preferable compounds that can be generated include acetone, diethyl ketone, methyl ethyl ketone, and methyl isobutyl ketone. Of these, acetone is the most preferable compound because it can increase the yield and shorten the reaction time.

The mixing ratio of the water-ketone mixed solvent in the present invention is not particularly limited, but the preferable water / ketone mixing ratio (volume ratio) is 1/9 to 9/1 because the reaction can be completed in a short time. And more preferably 3/7 to
It is 7/3.

Phase Transfer Catalyst A phase transfer catalyst is a catalyst having a function of promoting a reaction between substrates existing in different phases. As the phase transfer catalyst in the present invention, a quaternary ammonium salt, a quaternary phosphonium salt,
Any conventionally known one such as crown ether and cryptand can be used. Preferred phase transfer catalysts in the present invention include organic salt phase transfer catalysts such as quaternary ammonium salts and quaternary phosphonium salts, which are suitable for nucleophilic substitution reaction of halogen ions with phenoxy ions.

Specific examples of the quaternary ammonium salt include tetra-n-butylammonium fluoride, tetraethylammonium fluoride, tetramethylammonium chloride, tetraethylammonium chloride,
Tetrapropyl ammonium chloride, tetra-n-
Butylammonium chloride, tetra-n-amylammonium chloride, trimethylethylammonium chloride, trimethylbenzylammonium chloride, triethylbenzylammonium chloride, trioctylmethylammonium chloride, dimethyldi-
n-butylammonium chloride, dimethylbenzylphenylammonium chloride, distearyldimethylammonium chloride, benzyltri-n-butylammonium bromide, cetyldimethylethylammonium bromide, n-decyltrimethylammonium bromide, distearyldimethylammonium bromide, n-hexadecyltrimethyl Ammonium bromide, phenyltrimethylammonium bromide, tetra-n-butylammonium bromide, tetraethylammonium bromide, tetramethylammonium bromide, tetra-n-propylammonium bromide, trimethylvinylammonium bromide, ethyltrimethylammonium iodide, ethyltri-n-
Propyl ammonium iodide, phenyl triethyl ammonium iodide, phenyl trimethyl ammonium iodide, tetra-n-amyl ammonium iodide,
Tetra-n-butylammonium iodide, tetraethylammonium iodide, tetra-n-hexylammonium iodide, tetramethylammonium iodide,
Triethylbenzylammonium iodide, benzyltrimethylammonium hydroxide, n-hexadecyltrimethylammonium hydroxide, phenyltrimethylammonium hydroxide, tetra-n-butylammonium hydroxide, tetra-n-decylammonium hydroxide, tetra-ethylammonium hydroxide Side, tetramethylammonium hydroxide, tetra-n-propylammonium hydroxide, trimethylbenzylammonium hydroxide, benzyltrimethylammonium tribromide, tetra-n-butylammonium bromoiodide, tetraethylammonium perchlorate and tetramethylammonium sulfate. There is.

Specific examples of the quaternary phosphonium salt include allyltriphenylphosphonium bromide, allyltriphenylphosphonium chloride, benzyltriphenylphosphonium chloride, n-butyltriphenylphosphonium bromide, chloromethyltriphenylphosphonium chloride, 4-ethoxybenzyltrichloride. Phenylphosphonium bromide, ethyltriphenylphosphonium bromide, n-hexyltriphenylphosphonium bromide,
Methyltriphenylphosphonium iodide, tetra-n
-Butylphosphonium bromide, tetraphenylphosphonium chloride and tetraphenylphosphonium tetraphenylborate.

Preferred examples of these phase transfer catalysts are quaternary ammonium salts, because of their ease of purification after the reaction.
In particular tetramethylammonium bromide, tetraethylammonium bromide, tetra-n-propylammonium chloride, tetra-n-propylammonium bromide, tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, tributylbenzylammonium chloride and tributylbenzylammonium. Bromide and the like are preferred.

The preferred amount of the phase transfer catalyst used in the present invention is 0.01 to 50 mol%, and more preferably 1 to 20 mol% with respect to 1 mol of the phenolic hydroxyl group of the starting phenol. . When the amount of the phase transfer catalyst used is less than 0.01 mol%, the reaction time becomes long,
Even if it is used in an amount of 50 mol% or more, there is no great difference in the effect, and there is a risk of economic disadvantage.

The phase transfer catalyst may be prepared by using a commercially available phase transfer catalyst as it is, or by reacting an amine or phosphine with an acid such as a halide in the system.
You may use it as a quaternary ammonium salt or a quaternary phosphonium salt.

There is no particular limitation on the method of adding the phase transfer catalyst, as long as it is present in an amount sufficient to promote the reaction after the start of the reaction, and a predetermined amount of the entire amount is added to the reaction solution before the reaction. Alternatively, it may not be added before the reaction, or part of a predetermined amount may be added in advance and the rest may be added during the reaction.

○ Reaction Conditions The preferable reaction charge ratio of the phenols and the alkenyl halides in the present invention cannot be set to a uniform condition depending on the kind and reactivity of the alkenyl halides, but it is not limited to 1 mol of the phenolic hydroxyl group of the phenols. On the other hand, it is 1 to 3 mol of alkenyl halide, and more preferably 1 to 1.5 mol.

Further, the preferable charging ratio of phenols and alkalis in the reaction system is 1 to 3 moles of alkali to 1 mole of phenolic hydroxyl group of phenols,
It is more preferably 1 to 1.5 mol.

The reaction temperature and reaction time cannot be uniformly set because they differ depending on the type of ketone used, the type and amount of phase transfer catalyst, and the type and amount of alkenyl halide, but usually the temperature is from room temperature to 150 ° C. 0.5-2
It may be set within a range of 4 hours, more preferably 40
The reaction is carried out at a temperature of -100 ° C for 1-12 hours.

The reaction can be carried out under any conditions of reduced pressure, normal pressure and increased pressure. The reaction atmosphere is not particularly limited, and may be air or an atmosphere of an inert gas such as nitrogen or argon.

Separation and Purification After producing the alkenyl phenyl ethers as described above, the product can be extracted by a conventional method and used as it is as various synthetic raw materials, but if necessary, it may be washed with water or the like. The extract may be purified by the general purification method of.

[0035]

[Examples and Comparative Examples] Next, according to Examples and Comparative Examples,
The present invention will be described more specifically.

Example 1 A 300 ml glass four-necked flask equipped with a stirrer, a reflux tube, a thermometer and a dropping funnel was used for 4-
tert-Butylphenol 30.0 g (0.20 mol), 96% sodium hydroxide 9.2 g (0.22 mol), tetra-n-butylammonium bromide 3.2
90 g of g (0.01 mol) and a mixed solvent of acetone and water [acetone: water = 1: 1 (volume ratio)] was charged and heated and stirred. After the internal temperature reached 60 ° C., 21.7 g (0.24 mol) of methallyl chloride was slowly added dropwise, and after the addition was completed, the reaction was further performed at an internal temperature of 60 ± 3 ° C. for 2 hours. After completion of the reaction, the aqueous layer was neutralized with hydrochloric acid, extracted with dichloromethane, and the dichloromethane layer was analyzed by gas chromatography.
-Butylphenol has disappeared completely. As described above, based on the production amount when the total amount of 4-tert-butylphenol used as the reaction raw material is converted,
The desired product, 4-tert-butylphenylmethallyl ether, was obtained in a yield of 98.3%. (Hereinafter, the yield of the target product is shown based on the production amount when the total amount of the phenols used as the reaction raw material is converted.)

[0036]

Example 2 In a 300 ml glass four-necked flask equipped with a stirrer, a reflux tube, a thermometer and a dropping funnel, 29.7 g (0.13 mol) of bisphenol A and 12.1 g (0.1% of 0.2%) of 96% sodium hydroxide were added. 29 mol), tetra-n
-Butyl ammonium bromide 4.2 g (0.013 mol) and a mixed solvent of acetone and water [acetone: water =
1: 1 (volume ratio)] 120 ml was charged and heated and stirred. After the internal temperature reached 60 ° C, methallyl chloride 2
9.0 g (0.32 mol) was slowly added dropwise, and after the addition was completed, the reaction was further performed at an internal temperature of 60 ± 3 ° C. for 2 hours. After completion of the reaction, the aqueous layer portion was neutralized with hydrochloric acid, extracted with dichloromethane, and the dichloromethane layer was analyzed by gas chromatography. As a result, the starting materials bisphenol A and bisphenol A monomethallyl ether were not present at all. As described above, the target product, bisphenol A
Dimethallyl ether was obtained in a yield of 98.7%.

[0037]

Example 3 Of the charged amounts of Example 2, the amount of tetra-n-butylammonium bromide was 2.1 g (0.0066).
Mol) and the reaction time was 4.5 hours, and the reaction was performed in the same manner as in Example 2, and the treatment after the completion of the reaction was also performed. As a result of analysis by gas chromatography, the raw material bisphenol A and the intermediate bisphenol A monomethallyl ether were completely disappeared. As described above, the target product, bisphenol A dimethallyl ether, was obtained in a yield of 97.4%.

[0038]

[Example 4] In the charge of Example 2, the amount of tetra-n-butylammonium bromide was 2.1 g (0.0066 mol), and the reaction solvent was a mixed solvent of methyl ethyl ketone and water [methyl ethyl ketone: water = 1: 1. 1 (volume ratio)],
The reaction was performed in the same manner as in Example 2 except that the reaction time was 6 hours, and the treatment after the reaction was also performed in the same manner. As a result of analysis by gas chromatography, the raw material bisphenol A and the intermediate bisphenol A monomethallyl ether were completely disappeared. As above
The target compound, bisphenol A dimethallyl ether, was added to 9
Obtained in a yield of 7.2%.

[0039]

Example 5 Among the charging materials of Example 2, the amount of tetra-n-butylammonium bromide was 2.1 g (0.0066 mol), and the reaction solvent was a mixed solvent of diethyl ketone and water [diethyl ketone: water = 1: 1 (volume ratio)], and the reaction was performed in the same manner as in Example 2 except that the reaction time was 8 hours, and the treatment after completion of the reaction was also performed. As a result of analysis by gas chromatography, bisphenol A as a raw material
And the intermediate bisphenol A monomethallyl ether had completely disappeared. As described above, 97.0% of the target product, bisphenol A dimethallyl ether, was added.
It was obtained in a yield of.

[0040]

[Example 6] In the charges of Example 2, the amount of tetra-n-butylammonium bromide was 2.1 g (0.0066 mol), and the reaction solvent was a mixed solvent of methyl isobutyl ketone and water [methyl isobutyl ketone: Example 2 except that water = 1: 1 (volume ratio)] and the reaction time was 10 hours.
The reaction was carried out in the same manner as above, and the treatment after the reaction was also carried out in the same manner. As a result of analysis by gas chromatography, the raw material bisphenol A and the intermediate bisphenol A monomethallyl ether were completely disappeared. As described above, the target product, bisphenol A dimethallyl ether, was obtained in a yield of 96.5%.

[0041]

[Example 7] Example 7 except that the kind and amount of the phase-transfer catalyst used in Example 2 was 1.8 g (0.0066 mol) of tetra-n-butylammonium chloride and the reaction time was 6 hours. The same procedure as in 2 was performed, and the treatment after the reaction was also performed in the same manner. As a result of analysis by gas chromatography, the raw material bisphenol A and the intermediate bisphenol A monomethallyl ether were completely disappeared. As described above, the target product, bisphenol A dimethallyl ether, was obtained in a yield of 97.7%.

[0042]

Example 8 Example 2 was repeated except that the kind and amount of the phase transfer catalyst in the charge of Example 2 was 2.1 g (0.0066 mol) of tributylbenzylammonium chloride and the reaction time was 7 hours. The same method was used, and the treatment after the reaction was also performed in the same manner. As a result of analysis by gas chromatography, the raw material bisphenol A and the intermediate bisphenol A monomethallyl ether were completely disappeared. As described above, the target product, bisphenol A dimethallyl ether, was obtained in a yield of 97.3%.

[0043]

[Example 9] Among the charged materials of Example 2, the amount of tetra-n-butylammonium bromide was 2.1 g (0.0066 mol), and the reaction solvent was a mixed solvent of acetone and water [acetone: water = 7: 3 (volume ratio)] and the reaction time was 12 hours, the reaction was carried out in the same manner as in Example 2, and the treatment after the completion of the reaction was also carried out in the same manner. As a result of analysis by gas chromatography, the raw material bisphenol A and the intermediate bisphenol A monomethallyl ether were completely disappeared. As described above, the target product, bisphenol A dimethallyl ether, was obtained in a yield of 99.1%.

[0044]

Example 10 Of the charges of Example 2, the amount of tetra-n-butylammonium bromide was 2.1 g (0.0066).
Mol), the reaction solvent was a mixed solvent of acetone and water [acetone: water = 4: 6 (volume ratio)], and the reaction time was 6 hours. The treatment after completion of the reaction was performed in the same manner. As a result of analysis by gas chromatography, the raw material bisphenol A and the intermediate bisphenol A monomethallyl ether were completely disappeared. As described above, the target product, bisphenol A dimethallyl ether, was obtained in a yield of 96.4%.

[0045]

[Example 11] The reaction was carried out in the same manner as in Example 2 except that the amount and the kind of the raw material phenol used in Example 2 were 26.0 g (0.13 mol) of bisphenol F.
The treatment after completion of the reaction was performed in the same manner. As a result of analysis by gas chromatography, the raw material bisphenol F and the intermediate bisphenol F monomethallyl ether were completely disappeared. As described above, the target product, bisphenol F dimethallyl ether, was obtained in a yield of 98.2%.

[0046]

[Example 12] The type and amount of alkenyl halide in the charge of Example 2 was 24.5 g (0.3
2 mol) and the reaction temperature was 50 ± 3 ° C., the reaction was carried out in the same manner as in Example 2, and the treatment after the completion of dropping was also carried out in the same manner. As a result of analysis by gas chromatography, the raw material bisphenol A and the intermediate bisphenol A monoallyl ether were completely disappeared. As described above, the target product, bisphenol A
The diallyl ether was obtained in a yield of 97.2%.

[0047]

Example 13 The type and amount of the phase transfer catalyst in the charge of Example 1 was changed to tetra-n-butylphosphonium bromide 3.
The reaction was performed in the same manner as in Example 1 except that the amount was 4 g (0.01 mol) and the reaction time was 3 hours, and the treatment after the completion of the reaction was also performed. As a result of analysis by gas chromatography, 4-tert-butylphenol as a raw material was completely lost. As described above, the target 4-tert-butylphenylmethallyl ether
Obtained in a yield of 8.1%.

[0048]

[Comparative Example] The reaction was carried out in the same manner as in Example 1 except that tetra-n-butylammonium bromide was removed from the charge of Example 1, and the treatment after completion of the reaction was also carried out in the same manner. As a result of analysis by gas chromatography, 4-
12.3% tert-butylphenol remains,
The yield of the desired product, 4-tert-butylphenylmethallyl ether, was 78.1%.

[0049]

INDUSTRIAL APPLICABILITY The production method of the present invention makes it possible to produce alkenyl phenyl ethers in a higher yield than ever before by reacting phenols with alkenyl halides. It is extremely useful.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kaoru Kimura 1-1 Funami-cho, Minato-ku, Nagoya-shi, Aichi Toagosei Chemical Industry Co., Ltd. Nagoya Research Institute

Claims (1)

[Claims] 1. A phase transfer catalyst and an alkali are present,
A method for producing alkenyl phenyl ethers, which comprises reacting a phenol and an alkenyl halide in a water-ketone mixed solvent.