JPH0134215B2 - - Google Patents
Info
- Publication number
- JPH0134215B2 JPH0134215B2 JP16141581A JP16141581A JPH0134215B2 JP H0134215 B2 JPH0134215 B2 JP H0134215B2 JP 16141581 A JP16141581 A JP 16141581A JP 16141581 A JP16141581 A JP 16141581A JP H0134215 B2 JPH0134215 B2 JP H0134215B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- hydroxide
- yield
- mol
- pentanone
- 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
Links
- -1 alkali metal alkoxide Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 4
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical class CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 2
- HNIGAMRCLLBTGL-UHFFFAOYSA-N 4-anilino-4-methylpentan-2-one Chemical compound CC(=O)CC(C)(C)NC1=CC=CC=C1 HNIGAMRCLLBTGL-UHFFFAOYSA-N 0.000 description 2
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JXWCSPLQPDHCAU-UHFFFAOYSA-N 4-(4-chloroanilino)-4-methylpentan-2-one Chemical compound CC(=O)CC(C)(C)NC1=CC=C(Cl)C=C1 JXWCSPLQPDHCAU-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- KSPSUKXIIZUBGM-UHFFFAOYSA-N 4-methyl-4-(4-methylanilino)pentan-2-one Chemical compound CC(=O)CC(C)(C)NC1=CC=C(C)C=C1 KSPSUKXIIZUBGM-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000000654 additive Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 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
- 239000000543 intermediate Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- ILCQYORZHHFLNL-UHFFFAOYSA-N n-bromoaniline Chemical compound BrNC1=CC=CC=C1 ILCQYORZHHFLNL-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- RRHNGIRRWDWWQQ-UHFFFAOYSA-N n-iodoaniline Chemical compound INC1=CC=CC=C1 RRHNGIRRWDWWQQ-UHFFFAOYSA-N 0.000 description 1
- GCULWAWIZUGXTO-UHFFFAOYSA-N n-octylaniline Chemical compound CCCCCCCCNC1=CC=CC=C1 GCULWAWIZUGXTO-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 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】
本発明は一般式（）
（式中、ＸおよびＹは同一または異なつて水素
原子、ハロゲン原子、C1〜8のアルキル基またはア
ルコキシ基を示す）
で示される４―アリールアミノ―４―メチル―２
―ペンタノン類の製造法に関する。[Detailed Description of the Invention] The present invention relates to the general formula () (In the formula, X and Y are the same or different and represent a hydrogen atom, a halogen atom, a C1-8 alkyl group or an alkoxy group)
- Concerning the production method of pentanones.
本発明の目的化合物である４―アリールアミノ
―４―メチル―２―ペンタノン類は、医薬、農
薬、高分子添加剤およびゴム用老化防止剤等の有
用な中間体であり、このものは、従来より、アニ
リン類とメシチルオキシドとを無触媒下で反応さ
せることにより合成されていた。 4-arylamino-4-methyl-2-pentanones, which are the target compounds of the present invention, are useful intermediates for pharmaceuticals, agricultural chemicals, polymer additives, anti-aging agents for rubber, etc. It was synthesized by reacting anilines and mesityl oxide without a catalyst.
しかしながら従来法においては、反応温度40〜
50℃の加熱下で120時間もの長時間反応せしめて
も、収率はせいぜい約25％であり、しかも不純物
もかなり生成し、消費したアニリン類換算での収
率は約50％と低く、工業的には甚だ問題の多い製
造方法であつた。 However, in the conventional method, the reaction temperature is 40~
Even if the reaction is carried out for as long as 120 hours under heating at 50°C, the yield is only about 25% at most, and a considerable amount of impurities is produced. The manufacturing method was extremely problematic.
本発明らは、かかる従来法のもつ欠点を改良
し、アニリン類とメシチルオキシドから工業的有
利に、４―アリールアミノ―４―メチル―２―ペ
ンタノン類を製造する方法について鋭意検討した
結果、特定の触媒を使用することにより、常温下
でも短時間に、しかも高収率で目的物が得られ、
更には不純物の生成も少ないなど工業的に非常に
すぐれた効果が得られることを見出し、本発明に
至つた。 The present inventors have made intensive studies on a method for producing 4-arylamino-4-methyl-2-pentanones from anilines and mesityl oxide with industrial advantage by improving the drawbacks of such conventional methods. By using a specific catalyst, the desired product can be obtained in a short time and in high yield even at room temperature.
Furthermore, the present inventors have discovered that very excellent industrial effects such as less generation of impurities can be obtained, leading to the present invention.
すなわち本発明は、一般式（）
（式中、ＸおよびＹは前記と同じ意味を有す
る）
で示されるアニリン類とメシチルオキシドとをア
ルカリ金属アルコキシドまたは四級アンモニウム
ハイドロオキシドの存在下に反応させることを特
徴とする前記一般式（）で示される４―アリー
ルアミノ―４―メチル―２―ペンタノン類の製造
法である。 That is, the present invention provides general formula () (wherein, X and Y have the same meanings as above) The above general formula ( ) is a method for producing 4-arylamino-4-methyl-2-pentanones.
本発明において用いられるアニリン類として
は、アニリン、クロルアニリン、ブロムアニリ
ン、ヨードアニリン、トルイジン、キシリジン、
ブチルアニリン、オクチルアニリン、フエネチジ
ン、オクトキシアニリン等が例示される。 The anilines used in the present invention include aniline, chloraniline, bromoaniline, iodoaniline, toluidine, xylidine,
Examples include butylaniline, octylaniline, phenetidine, octoxyaniline, and the like.
また本発明で用いられるアルカリ金属アルコキ
シドとしてはナトリウムメトキシド、ナトリウム
エトキシド、ナトリウムブトキシド、カリウムエ
トキシド、カリウムブトキシド等が例示される。
また、四級アンモニウムハイドロオキシドとして
はトリメチルベンジルアンモニウムハイドロオキ
シド、トリエチルベンジルアンモニウムハイドロ
オキシド、テトラブチルアンモニウムハイドロオ
キシド等が挙げられるが、実質的に四級アンモニ
ウムハイドロキシドであれば良く、例えば、四級
アンモニウムハライド塩と金属水酸化物の組合わ
せでもよい。この場合に用いられる金属水酸化物
としては水酸化ナトリウム、水酸化カルシユウ
ム、水酸化カリウムなどの一般的な金属水酸化物
で十分であり、特に限定されない。 Examples of the alkali metal alkoxide used in the present invention include sodium methoxide, sodium ethoxide, sodium butoxide, potassium ethoxide, potassium butoxide, and the like.
Examples of the quaternary ammonium hydroxide include trimethylbenzylammonium hydroxide, triethylbenzylammonium hydroxide, and tetrabutylammonium hydroxide, but any substantially quaternary ammonium hydroxide may be used, such as quaternary ammonium hydroxide. A combination of halide salt and metal hydroxide may also be used. The metal hydroxide used in this case is not particularly limited, and common metal hydroxides such as sodium hydroxide, calcium hydroxide, and potassium hydroxide are sufficient.
かかる触媒の使用量は、通常アニリン類に対し
て0.001〜１モル％、好ましくは0.005〜0.5モル％
である。 The amount of such catalyst used is usually 0.001 to 1 mol%, preferably 0.005 to 0.5 mol% based on the aniline.
It is.
以下実施例により本発明を説明する。 The present invention will be explained below with reference to Examples.
実施例 １
300mlのフラスコにアニリン93ｇ（１モル）、メ
シチルオキシド98ｇ（１モル）およびトリメチル
ベンジルアンモニウムハイドロオキシドの40％水
溶液８ｇ（0.02モル）を仕込み、室温下で８時間
撹拌した。この反応マスを水洗した後、減圧蒸留
により、沸点94〜97℃／２mmHgの４―アニリノ
―４―メチル―２―ペンタノン174.6ｇを得た。Example 1 A 300 ml flask was charged with 93 g (1 mol) of aniline, 98 g (1 mol) of mesityl oxide, and 8 g (0.02 mol) of a 40% aqueous solution of trimethylbenzylammonium hydroxide, and stirred at room temperature for 8 hours. After washing this reaction mass with water, 174.6 g of 4-anilino-4-methyl-2-pentanone with a boiling point of 94 to 97°C/2 mmHg was obtained by distillation under reduced pressure.
収率 91.4％
比較例 １
トリメチルベンジルアンモニウムハイドロオキ
シドを使用しない以外は実施例１と全く同一の仕
込を行い、50〜60℃の加熱下で120時間反応を行
い、実施例１と同様な処理を行い４―アニリノ―
４―メチル―２―ペンタノン46.8ｇを得た。収率
24.5％
実施例 ２
トリメチルベンジルアンモニウムハイドロオキ
シドの代わりにナトリウムメチラート2.7ｇ
（0.05モル）を使用し、実施例１と同様な操作を
行つて４―アニリノ―４―メチル―２―ペンタノ
ン173.2ｇを得た。Yield: 91.4% Comparative Example 1 The same preparation as in Example 1 was carried out except that trimethylbenzylammonium hydroxide was not used, the reaction was carried out under heating at 50 to 60°C for 120 hours, and the same treatment as in Example 1 was carried out. Action 4-Anilino-
46.8 g of 4-methyl-2-pentanone was obtained. yield
24.5% Example 2 2.7g of sodium methylate instead of trimethylbenzylammonium hydroxide
(0.05 mol) and the same operation as in Example 1 was performed to obtain 173.2 g of 4-anilino-4-methyl-2-pentanone.
収率 90.7％
実施例 ３
トリメチルベンジルアンモニウムハイドロオキ
シドの代わりにトリエチルベンジルアンモニウム
クロリド1.1ｇ（0.005モル）、水20ｇおよび苛性
ソーダ0.3ｇを仕込み、実施例１と同様な操作を
行つて４―アニリノ―４―メチル―２―ペンタノ
ン176.3ｇを得た。Yield: 90.7% Example 3 In place of trimethylbenzylammonium hydroxide, 1.1 g (0.005 mol) of triethylbenzylammonium chloride, 20 g of water, and 0.3 g of caustic soda were charged, and the same operation as in Example 1 was performed to obtain 4-anilino-4. -Methyl-2-pentanone 176.3g was obtained.
収率 92.3％
実施例 ４
アニリンの代わりにｐ―トルイジン117ｇ（１
モル）を使用し、実施例１と同様な操作を行つ
て、沸点110〜114℃／２mmHgの４―（ｐ―トリ
ルアミノ）―４―メチル―２―ペンタノン192.4
ｇを得た。収率 89.5％
実施例 ５
アニリンの代わりに混合キシリジン121ｇ（１
モル）を使用し、実施例３と同様な操作を行つ
て、沸点127〜133℃／２mmHgの４―キシリルア
ミノ―４―メチル―２―ペンタノン189.4ｇを得
た。収率 86.5％
実施例 ６
アニリンの代わりにｐ―フエネチジン137ｇ
（１モル）を使用し、実施例３と同様な操作を行
つて、沸点141〜147℃／２mmHgの４―（ｐ―フ
エネチジノアミノ）―４―メチル―２―ペンタノ
ン213.1ｇを得た。Yield 92.3% Example 4 117g (1
4-(p-tolylamino)-4-methyl-2-pentanone with a boiling point of 110 to 114°C/2 mmHg was prepared using the same procedure as in Example 1.
I got g. Yield 89.5% Example 5 Mixed xylidine 121g (1
189.4 g of 4-xylylamino-4-methyl-2-pentanone having a boiling point of 127-133° C./2 mmHg was obtained by carrying out the same operation as in Example 3. Yield 86.5% Example 6 137g of p-phenetidine instead of aniline
(1 mol) and the same operation as in Example 3 was performed to obtain 213.1 g of 4-(p-phenetidinoamino)-4-methyl-2-pentanone with a boiling point of 141-147°C/2 mmHg. .
収率 90.7％
実施例 ７
アニリンの代わりにｐ―クロルアニリン127.6
ｇ（１モル）を使用し、実施例３と同様な操作を
行つて、沸点126〜131℃／２mmHgの４―（ｐ―
クロルアニリノ）―４―メチル―２―ペンタノン
186.1ｇを得た。Yield 90.7% Example 7 p-chloroaniline 127.6 instead of aniline
g (1 mol) and carried out the same operation as in Example 3 to obtain 4-(p-
Chloranilino)-4-methyl-2-pentanone
186.1g was obtained.
収率 82.5％Yield 82.5%
Claims (1)
原子、ハロゲン原子、C1〜8のアルキル基またはア
ルコキシ基を示す） で示されるアニリン類とメシチルオキシドとを、
アルカリ金属アルコキシドまたは四級アンモニウ
ムハイドロオキシドの存在下に反応させることを
特徴とする一般式 （式中、ＸおよびＹは前記と同じ意味を有す
る） で示される４―アリールアミノ―４―メチル―２
―ペンタノン類の製造法。[Claims] 1. General formula (wherein, X and Y are the same or different and represent a hydrogen atom, a halogen atom, a C1-8 alkyl group or an alkoxy group) and mesityl oxide,
General formula characterized by reaction in the presence of an alkali metal alkoxide or quaternary ammonium hydroxide (wherein, X and Y have the same meanings as above) 4-arylamino-4-methyl-2
-Production method of pentanones.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16141581A JPS5862143A (en) | 1981-10-09 | 1981-10-09 | Preparation of 4-arylamino-4-methyl-2-pentanone compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16141581A JPS5862143A (en) | 1981-10-09 | 1981-10-09 | Preparation of 4-arylamino-4-methyl-2-pentanone compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5862143A JPS5862143A (en) | 1983-04-13 |
| JPH0134215B2 true JPH0134215B2 (en) | 1989-07-18 |
Family
ID=15734657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16141581A Granted JPS5862143A (en) | 1981-10-09 | 1981-10-09 | Preparation of 4-arylamino-4-methyl-2-pentanone compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5862143A (en) |
-
1981
- 1981-10-09 JP JP16141581A patent/JPS5862143A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5862143A (en) | 1983-04-13 |
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