JPS6039276B2 - Method for producing 1,3-dioxane derivative - Google Patents
Method for producing 1,3-dioxane derivativeInfo
- Publication number
- JPS6039276B2 JPS6039276B2 JP1154778A JP1154778A JPS6039276B2 JP S6039276 B2 JPS6039276 B2 JP S6039276B2 JP 1154778 A JP1154778 A JP 1154778A JP 1154778 A JP1154778 A JP 1154778A JP S6039276 B2 JPS6039276 B2 JP S6039276B2
- Authority
- JP
- Japan
- Prior art keywords
- producing
- general formula
- dioxane derivative
- dioxane
- compound
- 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
Description
本発明は１，３ージオキサン誘導体の新規な製造方法に
関し、詳しくは、一般式〔１〕（式中、Ｒ，，Ｒ２，及
びＲ３は低級ァルキル基を示す。
）で表わされる５ーアシルメルドラム酸又はその同族化
合物を加熱分解することからなる一般式The present invention relates to a novel method for producing 1,3-dioxane derivatives, and more specifically, 5-acyl Meldrum represented by the general formula [1] (wherein R, R2, and R3 represent lower alkyl groups). General formula consisting of thermal decomposition of an acid or its homologous compound
〔０〕（式中、
Ｒ，，Ｒ２，及びＲ３は前記と同一の意味を有する。
）で表わされる４ーアルキルー２，２ージアルキル−１
．３ージオキセンー６ーオンの製造方法に関するもので
ある。本発明方法によって得られる一般式[0] (in the formula,
R, , R2, and R3 have the same meanings as above. ) 4-alkyl-2,2-dialkyl-1
．． This invention relates to a method for producing 3-dioxen-6-one. General formula obtained by the method of the present invention
〔０〕で表わ
される化合物は、医薬、農薬等の中間体として有用な化
合物であるが、その工業的に有利な製造方法はあまり知
られていない。
公知の方法としては、一般式The compound represented by [0] is a compound useful as an intermediate for medicines, agricultural chemicals, etc., but its industrially advantageous production method is not well known. As a known method, the general formula
〔０〕においてＲ，，Ｒ２
，及びＲ３はメチル基である化合物の製造方法として、
ジクテンとアセトンとをｐートルェンスホルン酸の存在
下で反応させて４−メチル−２，２−ジメチル−１，３
ージオキセン−６ーオンを製造する方法がジヤーナルオ
ブ アメリカン ケミカル ソサイアティー １９５２
王７準巻６３０５頁に記載されているのみであり、４位
のアルキル基がエチル、プロピル、ブチル基等である１
，３ージオキセンー６−オン類の製造法は知られていな
い。該既知製造法の原料化合物であるジクテンはその反
応性の面から種々の合成原料として用いられているが、
毒性、刺激性等が強く、工業的な原料としては好ましく
ない。しかしながら、本発明方法における原料化合物で
ある４−アシルメルドラム酸等は刺激性のない安全性の
高い化合物であって、メルドラム酸等をアシル化するこ
とにより、高収率で安価に得られる為、工業的な合成原
料化合物として有利である。本発明方法の実施にあたっ
ては、一般式〔１〕で表わされる５−アシルメルドラム
酸等を、融点以上の温度、通常１００〜１２０ｑｏに３
び分〜１時間加熱する。
室温に冷却後、生成物を適当な有機溶媒に溶解し、アル
カリ水溶液、水等で洗浄後乾燥し、溶媒を留去すれば一
般式〔ロ）で表わされる４ーアルキル−２，２−ジアル
キルー１，３ージオキセン−６−オンが得られる。次に
実施例を挙げて本発明方法について更に詳しく説明する
。実施例 １
４ーエチルー２，２−ジメチルー１，３ージオキセー４
ーエンー６ーオン２，２ージメチルー５ーブロピオニル
ー１，３ージオキサンー４，６ージオンｌｏｇを１．２
０つ○で１時間加熱し、室温に冷却した後、生成した油
状物をクロロホルムに溶解してＩＮ−ＮａＯＨで洗浄し
、クロロホルム層を無水硫酸マグネシウムで乾燥した。
溶媒を減圧で蟹去し残液を真空蒸留して無色透明の目的
物５．鶴を得た。ｂ，ｐ，〇，２脚Ｈｇ６５〜６７。実
施例 ２
２，２，４−トリメチルー１，３ージオキセ−４−工ン
ー６ーオン５ーアセチルー２，２−ジメチル−１，３−
ジオキサンー４，６ージオン１５ｇを１００００で３０
分加熱し、室温に冷却した後、生成した油状物をクロロ
ホルムに溶解してＩＮ−ＮａＯＨで洗浄し、クロロホル
ム層を無水硫酸マグネシウムで乾燥した。
溶媒を減圧で蟹去し、残液を真空蒸留して無色透明の目
的物６．鴇を得た。ｂ，ｐ，６側Ｈｇ ７０〜７〆ＣR,,R2 in [0]
, and R3 is a methyl group, as a method for producing a compound,
4-Methyl-2,2-dimethyl-1,3 was obtained by reacting dictene and acetone in the presence of p-toluensphoric acid.
A method for producing -dioxene-6-one was published in the Journal of the American Chemical Society in 1952.
It is only described in Wang 7 Subvol. 6305, and the alkyl group at the 4th position is ethyl, propyl, butyl group, etc.
, 3-dioxen-6-ones are not known. Dictene, which is a raw material compound in the known production method, is used as a raw material for various synthetics due to its reactivity.
It is highly toxic and irritating, making it undesirable as an industrial raw material. However, 4-acylmeldrum's acid, etc., which are the raw material compounds in the method of the present invention, are non-irritating and highly safe compounds, and can be obtained in high yield and at low cost by acylating Meldrum's acid, etc. , is advantageous as an industrial synthetic raw material compound. In carrying out the method of the present invention, 5-acyl Meldrum's acid etc. represented by the general formula [1] are heated at a temperature higher than the melting point, usually at 100 to 120 qo.
Heat for about 1 minute to 1 hour. After cooling to room temperature, the product is dissolved in a suitable organic solvent, washed with an aqueous alkaline solution, water, etc., and dried. The solvent is distilled off to obtain 4-alkyl-2,2-dialkyl-1 represented by the general formula (b). , 3-dioxen-6-one is obtained. Next, the method of the present invention will be explained in more detail with reference to Examples. Example 1 4-ethyl-2,2-dimethyl-1,3-dioxe 4
-en-6-one 2,2-dimethyl-5-propionyl-1,3-dioxane-4,6-dione log 1.2
After heating at 0 x 0 for 1 hour and cooling to room temperature, the resulting oil was dissolved in chloroform and washed with IN-NaOH, and the chloroform layer was dried over anhydrous magnesium sulfate. The solvent is removed under reduced pressure and the residual liquid is vacuum distilled to obtain a colorless and transparent target product.5. I got a crane. b, p, 〇, 2 legs Hg 65-67. Example 2 2,2,4-trimethyl-1,3-diox-4-ene-6-one 5-acetyl-2,2-dimethyl-1,3-
Dioxane-4,6-dione 15g is 10000 30
After heating for minutes and cooling to room temperature, the resulting oil was dissolved in chloroform and washed with IN-NaOH, and the chloroform layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residual liquid was vacuum distilled to obtain a colorless and transparent target product6. I got a tow. b, p, 6 side Hg 70~7〆C
Claims (1)
を示す。 ）で表わされる化合物を加熱分解することを特徴とする
一般式▲数式、化学式、表等があります▼ で表わされる化合物の製造方法。 ２ Ｒ＿２及びＲ＿３がメチル基である特許請求の範囲
第１項記載の製造方法。[Claims] 1. A compound represented by the general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1, R_2, and R_3 represent lower alkyl groups.) A method for producing compounds represented by the general formula ▲Mathematical formulas, chemical formulas, tables, etc.▼. 2. The manufacturing method according to claim 1, wherein R_2 and R_3 are methyl groups.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1154778A JPS6039276B2 (en) | 1978-02-06 | 1978-02-06 | Method for producing 1,3-dioxane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1154778A JPS6039276B2 (en) | 1978-02-06 | 1978-02-06 | Method for producing 1,3-dioxane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54106478A JPS54106478A (en) | 1979-08-21 |
| JPS6039276B2 true JPS6039276B2 (en) | 1985-09-05 |
Family
ID=11780977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1154778A Expired JPS6039276B2 (en) | 1978-02-06 | 1978-02-06 | Method for producing 1,3-dioxane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6039276B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61189522U (en) * | 1985-05-17 | 1986-11-26 | ||
| JPS63291494A (en) * | 1987-05-25 | 1988-11-29 | Ibiden Co Ltd | Surface mounting printed wiring board |
| JPS63198178U (en) * | 1987-06-11 | 1988-12-20 | ||
| JPH01143083U (en) * | 1988-03-28 | 1989-09-29 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112174929A (en) * | 2020-10-13 | 2021-01-05 | 台州市生物医化产业研究院有限公司 | Pyrolysis impurity of sitagliptin key intermediate, and preparation method and application thereof |
-
1978
- 1978-02-06 JP JP1154778A patent/JPS6039276B2/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61189522U (en) * | 1985-05-17 | 1986-11-26 | ||
| JPS63291494A (en) * | 1987-05-25 | 1988-11-29 | Ibiden Co Ltd | Surface mounting printed wiring board |
| JPS63198178U (en) * | 1987-06-11 | 1988-12-20 | ||
| JPH01143083U (en) * | 1988-03-28 | 1989-09-29 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54106478A (en) | 1979-08-21 |
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