JPH07577B2 - Method for producing anisaldehyde - Google Patents
Method for producing anisaldehydeInfo
- Publication number
- JPH07577B2 JPH07577B2 JP14209886A JP14209886A JPH07577B2 JP H07577 B2 JPH07577 B2 JP H07577B2 JP 14209886 A JP14209886 A JP 14209886A JP 14209886 A JP14209886 A JP 14209886A JP H07577 B2 JPH07577 B2 JP H07577B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- mol
- anisaldehyde
- parahydroxybenzaldehyde
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 26
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 14
- 230000018044 dehydration Effects 0.000 claims description 13
- 238000006297 dehydration reaction Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 230000001035 methylating effect Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 10
- 239000003513 alkali Substances 0.000 description 7
- 238000007069 methylation reaction Methods 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
- 229940031826 phenolate Drugs 0.000 description 3
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- DZXBHDRHRFLQCJ-UHFFFAOYSA-M sodium;methyl sulfate Chemical compound [Na+].COS([O-])(=O)=O DZXBHDRHRFLQCJ-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 ＜産業上の利用分野＞ 本発明は、香料、医薬、農薬、その他有機合成原料に重
要なアニスアルデヒドの製造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION <Industrial field of application> The present invention relates to a method for producing anisaldehyde, which is important for perfumes, pharmaceuticals, agricultural chemicals and other organic synthetic raw materials.
＜従来技術＞ 従来アニスアルデヒドの製造法としては、パラメトキシ
トルエンを出発物資とする方法が一般的である。例え
ば、酸化剤酸化法としては特公昭58−20947号、液相酸
素酸化法としては特公昭55−42974号、気相酸化法とし
ては特公昭58−4012号、電解酸化法としては特開昭55−
85682号公報にそれぞれ記載されている方法等が知られ
ている。<Prior Art> Conventionally, as a method for producing anisaldehyde, a method using paramethoxytoluene as a starting material has been generally used. For example, JP-B-58-20947 is used as an oxidizing agent oxidizing method, JP-B-55-42974 is used as a liquid-phase oxygen oxidizing method, JP-B-58-4012 is used as a gas-phase oxidizing method, and JP-A-58-4012 is used as an electrolytic oxidizing method. 55-
The methods and the like described in Japanese Patent Publication No. 85682 are known.
＜発明が解決しようとする問題点＞ しかしながら、酸化剤を用いる化学的酸化法は、酸化剤
を化学量論的に必要とし、経済的でない。また一度使用
した酸化剤を酸化して再使用する方法もあるが、設備費
が嵩み得策でない。<Problems to be Solved by the Invention> However, the chemical oxidation method using an oxidizing agent requires an oxidizing agent stoichiometrically and is not economical. There is also a method in which an oxidizing agent used once is oxidized and reused, but this is not a good measure because the equipment cost is high.
液相酸素酸化法は、比較的高価な触媒を使用するし、反
応率、選択率も低い為実用的でない。The liquid-phase oxygen oxidation method is not practical because it uses a relatively expensive catalyst and has a low reaction rate and selectivity.
電解酸化法は、倒鎖の酸化のみならず芳香核への求核置
換反応が併発する等副反応が多く、目的物が低収率でし
か得られず実用的な方法とは言い難い。また設備費も割
高となり、好ましくない。The electrolytic oxidation method has many side reactions such as nucleophilic substitution reaction on aromatic nucleus as well as oxidation of the inversion chain, and the target product can be obtained only in a low yield, so it is difficult to say that it is a practical method. In addition, the equipment cost becomes expensive, which is not preferable.
＜問題点を解決するための手段＞ 本発明者等は、前記のような欠点を改善するため、アニ
スアルデヒドの別の前躯体であるパラヒドロキシベンズ
アルデヒドをメチル化反応させて、アニスアルデヒドを
製造する方法について鋭意検討した所、高反応率、高選
択率で目的物を製造する方法を見出した。<Means for Solving the Problems> In order to improve the above-mentioned drawbacks, the present inventors produce anisaldehyde by subjecting parahydroxybenzaldehyde, which is another precursor of anisaldehyde, to a methylation reaction. As a result of diligent study on the method, a method for producing the target product with high reaction rate and high selectivity was found.
即ち、本発明は、パラヒドロキシベンズアルデヒドのメ
チル化に際しパラヒドロキシベンズアルデヒド１モルに
対し、ジメチル硫酸0.5〜５モルを用い、アルカリ水溶
液中、共沸脱水溶媒の共存下で反応および脱水すること
を特徴とするアニスアルデヒドの製造法である。That is, the present invention is characterized in that when methylating parahydroxybenzaldehyde, 0.5 to 5 mol of dimethylsulfate is used per 1 mol of parahydroxybenzaldehyde to carry out reaction and dehydration in an alkaline aqueous solution in the presence of an azeotropic dehydration solvent. This is a method for producing anisaldehyde.
パラヒドロキシベンズアルデヒドとジメチル硫酸は、化
学量論的にはパラヒドロキシベンズアルデヒド１モルに
対し、ジメチル硫酸0.5モルで反応すると考えられる。
しかしながら反応温度90℃以下では、ジメチル硫酸の２
個のメチル基の内１個しか有効に利用されない。従って
反応を90℃以下で実施するとパラヒドロキシベンズアル
デヒド１モルに対し毒性も強く高価なジメチル硫酸が１
モル以上必要となり得策とは言い難い。It is considered that parahydroxybenzaldehyde and dimethylsulfate react stoichiometrically with 0.5 mol of dimethylsulfate per mol of parahydroxybenzaldehyde.
However, if the reaction temperature is below 90 ° C
Only one of the methyl groups is effectively used. Therefore, if the reaction is carried out at 90 ° C or lower, 1 mol of parahydroxybenzaldehyde is mixed with 1 mol of expensive dimethyl sulfate, which is highly toxic and expensive.
It is difficult to say that it is a good idea because it requires more than a mole.
一方、ジメチル硫酸の滴下、熟成を50〜100℃、好まし
くは60〜90℃の比較的低温で実施（以下第１メチル化と
称す。）した後、反応温度を130℃、好ましくは150℃近
く迄上げる（以下第２メチル化と称す。）とジメチル硫
酸の２個のメチル基を有効に利用できる。ここで、第１
メチル化反応ではジメチル硫酸とフェノレートが、第２
メチル化反応ではモノメチル硫酸ナトリウム塩とフェノ
レートが反応していると考えられる。従って本発明の反
応の好ましい態様としては、最初50〜100℃の比較的低
温で実施するが、反応後半は、共沸脱水により水を系外
に留去し、反応温度を約130〜150℃まで上げジメチル硫
酸の２個のメチル基を有効に利用することである。On the other hand, after dripping and aging of dimethylsulfate at a relatively low temperature of 50 to 100 ° C, preferably 60 to 90 ° C (hereinafter referred to as first methylation), the reaction temperature is 130 ° C, preferably near 150 ° C. Up to the maximum (hereinafter referred to as the second methylation), two methyl groups of dimethylsulfate can be effectively used. Where the first
In the methylation reaction, dimethyl sulfate and phenolate are second
It is considered that monomethylsulfate sodium salt and phenolate react in the methylation reaction. Therefore, in a preferred embodiment of the reaction of the present invention, it is first carried out at a relatively low temperature of 50 to 100 ° C., but in the latter half of the reaction, water is distilled out of the system by azeotropic dehydration, and the reaction temperature is about 130 to 150 ° C. Is to effectively utilize the two methyl groups of dimethyl sulfate.
ジメチル硫酸は、アルカリ共存下ではアルカリと反応し
た芒硝等を副生するのでアルカリ量に応じて余分に加え
る必要がある。従ってジメチル硫酸の使用量としてはパ
ラヒドロキシベンズアルデヒド１モルに対し0.5〜５モ
ル、通常は0.5〜0.8モルが好ましい。Dimethylsulfuric acid produces a salt of Glauber's salt and the like that has reacted with alkali in the presence of an alkali, so it is necessary to add extra depending on the amount of the alkali. Therefore, the amount of dimethylsulfate used is preferably 0.5 to 5 mol, usually 0.5 to 0.8 mol, per 1 mol of parahydroxybenzaldehyde.
本発明の反応は、ジメチル硫酸とフェノレートとの間の
メチル化反応を優先するようにアルカリ水溶液中で行わ
れるがアルカリ使用量はパラヒドロキシベンズアルデヒ
ド１当量に対し、１〜10当量、通常は１〜1.6当量が好
ましい。The reaction of the present invention is carried out in an alkaline aqueous solution so as to give priority to the methylation reaction between dimethylsulfate and phenolate, but the amount of the alkali used is 1 to 10 equivalents, usually 1 equivalent to 1 equivalent of parahydroxybenzaldehyde. ~ 1.6 equivalents are preferred.
アルカリとしてはアルカリ金属、アルカリ土類金属の水
酸化物および炭酸塩が用いられるが、特に水酸化ナトリ
ウム、水酸化カリウムが好ましい。As the alkali, hydroxides and carbonates of alkali metals and alkaline earth metals are used, and sodium hydroxide and potassium hydroxide are particularly preferable.
アルカリの添加方法であるが第２メチル化の際少量のア
ルカリを添加すると、反応収率が更に向上する。また反
応系のPH低下を防ぎ、SUS系材質の保護にもなる。Although this is an alkali addition method, the reaction yield is further improved by adding a small amount of alkali during the second methylation. It also prevents the decrease of PH in the reaction system and protects SUS materials.
共沸脱水溶媒としては、ベンゼン、トルエン、キシレ
ン、クロルべンゼン、ヘプタン、メチルイソブチルケト
ン、酢酸エチル等を上げることができる。共沸脱水溶媒
は、反応前に添加しても良いし、共沸脱水前に添加して
も良い。Examples of the azeotropic dehydration solvent include benzene, toluene, xylene, chlorobenzene, heptane, methyl isobutyl ketone, ethyl acetate and the like. The azeotropic dehydration solvent may be added before the reaction or may be added before the azeotropic dehydration.
本発明に用いるパラベンズアルデヒドは、一般には精製
パラベンズアルデヒドであるが、未精製のまま使う事も
可能である。The parabenzaldehyde used in the present invention is generally purified parabenzaldehyde, but it is also possible to use it in an unpurified form.
例えば、特開昭55−81832記載の方法により、パラクレ
ゾールを空気酸化後、脱溶媒、酸析して得られる純度40
〜70％のパラベンズアルデヒドを用いても精製パラヒド
ロキシベンズアルデヒドを用いる場合と比較して遜色な
い反応成績を得ることができる。For example, according to the method described in JP-A-55-81832, after the air oxidation of para-cresol, desolvation, acid purity 40 obtained by
Even if ~ 70% parabenzaldehyde is used, comparable reaction results can be obtained as compared with the case of using purified parahydroxybenzaldehyde.
本発明の反応は通常、常圧で行われるが加圧あるいは減
圧下においても実施可能である。The reaction of the present invention is usually carried out at normal pressure, but it can also be carried out under increased pressure or reduced pressure.
本発明の方法の具体的な一実施態様は、パラヒドロキシ
ベンズアルデヒドを仕込み、アルカリ水溶液および共沸
脱水溶媒を添加し、所定温度に加熱する。次に撹拌下ジ
メチル硫酸を徐々に滴下し、後保温する。引き続き共沸
脱水により水を系外に留去し、反応温度を150℃近くに
迄上げる。尚、生成したアニスアルデヒドは、水洗浄
後、蒸留等、公知の方法により精製される。In a specific embodiment of the method of the present invention, para-hydroxybenzaldehyde is charged, an alkaline aqueous solution and an azeotropic dehydration solvent are added, and the mixture is heated to a predetermined temperature. Next, dimethylsulfuric acid is gradually added dropwise with stirring, and the temperature is kept afterward. Subsequently, water is distilled out of the system by azeotropic dehydration, and the reaction temperature is raised to near 150 ° C. The produced anisaldehyde is purified by a known method such as distillation after washing with water.
＜発明の効果＞ 本発明の方法によればパラヒドロキシベンズアルデヒド
よりアニスアルデヒドを高収率で製造することができ
る。<Effect of the Invention> According to the method of the present invention, anisaldehyde can be produced in a high yield from parahydroxybenzaldehyde.
次に本発明を実施例により更に詳細に説明する。Next, the present invention will be described in more detail with reference to Examples.
実施例１ パラヒドロキシベンズアルデヒド73.2g（0.6モル）に28
％水酸化ナトリウム溶液110g（0.77モル）キシレン33g
を加えた。この溶液を85℃に昇温した後ジメチル硫酸4
9.5g（0.39モル）を２時間かけて滴下し、１時間保温し
た。次に５時間共沸脱水し、水を反応系外に留去した。
最終反応温度は140℃であった。反応液を冷却し、水を
加えた後キシレン層をGC分析した所、アニスアルデヒド
は75.9g（0.56モル）生成した。Example 1 28% of 73.2 g (0.6 mol) of parahydroxybenzaldehyde
% Sodium hydroxide solution 110g (0.77mol) xylene 33g
Was added. The temperature of this solution was raised to 85 ° C and then dimethyl sulfate 4
9.5 g (0.39 mol) was added dropwise over 2 hours and kept warm for 1 hour. Next, azeotropic dehydration was carried out for 5 hours, and water was distilled out of the reaction system.
The final reaction temperature was 140 ° C. The reaction solution was cooled, water was added, and the xylene layer was analyzed by GC. As a result, 75.9 g (0.56 mol) of anisaldehyde was produced.
収率は、93.3％であった。The yield was 93.3%.
実施例２ パラヒドロキシベンズアルデヒド73.2g（0.6モル）に28
％水酸化ナトリウム溶液94g（0.66モル）キシレン33gを
加えた。Example 2 73.2 g (0.6 mol) of parahydroxybenzaldehyde
% Sodium hydroxide solution 94 g (0.66 mol) xylene 33 g was added.
この溶液を85℃に昇温した後、ジメチル硫酸49.5g（0.3
9モル）を２時間かけて滴下し、一時間保温した。次に2
8％水酸化ナトリウム溶液16g（0.11モル）を添加した
後、５時間共沸脱水し、水を反応系外に留去した。最終
反応温度は140℃であった。After heating the solution to 85 ° C, 49.5 g (0.3
(9 mol) was added dropwise over 2 hours and kept warm for 1 hour. Then 2
After 16 g (0.11 mol) of 8% sodium hydroxide solution was added, azeotropic dehydration was carried out for 5 hours, and water was distilled out of the reaction system. The final reaction temperature was 140 ° C.
反応液を冷却し、水を加えた後、キシレン層をGC分析し
た所アニスアルデヒドは78.9g（0.58モル）生成した。
収率は96.6％であった。The reaction solution was cooled, water was added, and the xylene layer was analyzed by GC. As a result, 78.9 g (0.58 mol) of anisaldehyde was produced.
The yield was 96.6%.
比較例 パラヒドロキシベンズアルデヒド73.2g（0.6モル）に28
％水酸化ナトリウム溶液110g（0.77モル）を加えた。こ
の溶液を85℃に昇温した後、ジメチル硫酸49.5g（0.39
モル）を２時間かけて滴下し、６時間保温した。Comparative example 73.2 g (0.6 mol) of para-hydroxybenzaldehyde gives 28
110 g (0.77 mol) of a% sodium hydroxide solution were added. After the temperature of this solution was raised to 85 ° C, 49.5 g (0.39
(Mol) was added dropwise over 2 hours and kept warm for 6 hours.
反応液を冷却し、水を加えた後、キシレン層をGC分析し
た所、アニスアルデヒドは、42.4g（0.31モル）生成し
た。収率は、52％であった。The reaction solution was cooled, water was added, and the xylene layer was analyzed by GC. As a result, 42.4 g (0.31 mol) of anisaldehyde was produced. The yield was 52%.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 徳丸 融 大分県大分市大字鶴崎2200番地 住友化学 工業株式会社内 (72)発明者 八幡 学 大分県大分市大字鶴崎2200番地 住友化学 工業株式会社内 (72)発明者 天野 末弘 兵庫県伊丹市森本２丁目247番地 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Toru Maru 2200 Tsurusaki, Oita, Oita, Sumitomo Chemical Co., Ltd. (72) Manabu Hachiman 2200, Tsurusaki, Oita, Oita Sumitomo Chemical Co., Ltd. 72) Inventor Suehiro Amano 2-247 Morimoto, Itami City, Hyogo Prefecture
Claims (2)
化に際し、パラヒドロキシベンズアルデヒド１モルに対
しジメチル硫酸0.5〜５モルを用い、アルカリ水溶液
中、共沸脱水溶媒の共存下で反応および脱水することを
特徴とするアニスアルデヒドの製造法1. When methylating parahydroxybenzaldehyde, 0.5 to 5 mol of dimethylsulfate is used for 1 mol of parahydroxybenzaldehyde to carry out reaction and dehydration in an alkaline aqueous solution in the presence of an azeotropic dehydration solvent. Method for producing anisaldehyde
い、次いで共沸脱水により水を系外に留去し、反応後半
を130〜150℃で行うことを特徴とする特許請求の範囲第
１項に記載のアニスアルデヒドの製造法2. The reaction is first carried out at a relatively low temperature of 50 to 100 ° C., then water is distilled out of the system by azeotropic dehydration, and the latter half of the reaction is carried out at 130 to 150 ° C. A method for producing anisaldehyde according to claim 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14209886A JPH07577B2 (en) | 1986-06-18 | 1986-06-18 | Method for producing anisaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14209886A JPH07577B2 (en) | 1986-06-18 | 1986-06-18 | Method for producing anisaldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62298546A JPS62298546A (en) | 1987-12-25 |
| JPH07577B2 true JPH07577B2 (en) | 1995-01-11 |
Family
ID=15307381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14209886A Expired - Lifetime JPH07577B2 (en) | 1986-06-18 | 1986-06-18 | Method for producing anisaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07577B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100456327B1 (en) * | 2001-07-11 | 2004-11-09 | 강원도 | Manufacturing Method of Anisaldehyde |
| CN105130773A (en) * | 2015-07-17 | 2015-12-09 | 天宁香料（江苏）有限公司 | Preparation method of p-methoxybenzaldehyde |
| CN115850033B (en) * | 2022-11-30 | 2024-04-02 | 重庆欣欣向荣精细化工有限公司 | Synthesis method of guaiacol |
-
1986
- 1986-06-18 JP JP14209886A patent/JPH07577B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62298546A (en) | 1987-12-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH07577B2 (en) | Method for producing anisaldehyde | |
| US4694110A (en) | Process for production of m-phenoxybenzyl alcohol | |
| US6441248B1 (en) | Preparation of biphenols by oxidative coupling of alkylphenols using copper catalyst | |
| WO2005110962A1 (en) | Process for producing adipic acid | |
| US6689921B2 (en) | Preparation of biphenols by oxidative coupling of alkylphenols using a recyclable copper catalyst | |
| EP0338666B1 (en) | Method for the preparation of 2,3,5-trimethylbenzoquinone | |
| US6410803B1 (en) | Process for the preparation of para-fluorophenol | |
| EP0193671B1 (en) | Separation of aniline and p-fluoroaniline | |
| JPH0745430B2 (en) | Method for producing 2,2-bis (hydroxymethyl) alkanoic acid | |
| JPH10265459A (en) | 1,2,3,6tetrahydro2,2,6,6methylpyridinn-oxyl | |
| JP2001206883A (en) | Process for producing 3,4-methylenedioxymandelic acid | |
| US4782190A (en) | Process for the preparation of 4-nitrophenetol | |
| KR100394582B1 (en) | Preparation method of catechol and hydroquinone | |
| JP2005187414A (en) | Method for producing 2-methyl-1,4-naphthoquinone | |
| JPS58120507A (en) | Continuous manufacture of hydrazine | |
| WO2024116184A1 (en) | Process for the preparation of 2-alkylsulfonyl substituted benzoic acid derivatives | |
| JPH06219999A (en) | Production of aminodiphenylether | |
| JPH072690B2 (en) | Method for producing 3-methyl-4-nitrophenol | |
| JPH0582376B2 (en) | ||
| JPH08151343A (en) | Method for producing 4-alkoxyphenol | |
| JPH07324050A (en) | Method for producing phenyl ethers | |
| McFadden et al. | A New Route to 2, 5-Dimethoxyphenylacetic Acid | |
| JPH08245462A (en) | Production of phenylphenol | |
| CN111548258A (en) | Use of sulfonyl type compounds as chlorination reagents | |
| JPH10130193A (en) | Production of 3'-hydroxyacetophenone |