JPS5944294B2 - Method for producing 3-phenoxybenzaldehydes - Google Patents
Method for producing 3-phenoxybenzaldehydesInfo
- Publication number
- JPS5944294B2 JPS5944294B2 JP51062449A JP6244976A JPS5944294B2 JP S5944294 B2 JPS5944294 B2 JP S5944294B2 JP 51062449 A JP51062449 A JP 51062449A JP 6244976 A JP6244976 A JP 6244976A JP S5944294 B2 JPS5944294 B2 JP S5944294B2
- Authority
- JP
- Japan
- Prior art keywords
- phenoxybenzaldehyde
- copper
- manufacturing
- phenol
- alkali metal
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は、３−フェノキシベンズアルデヒドまたはその
アセタールの製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 3-phenoxybenzaldehyde or its acetal.
たとえば、ＭｏｎａｔｓｈｅｆｔｅｆｕｒＣｈｅｍｉｅ
、Ｗｉｅｎ、６７（１９３５）、５９８〜６０９に示さ
れる３−フェノキシベンズアルデヒドの公知の製造方法
は、複雑であり、通常は、アルデヒドの収量が低い。For example, MonatsheftefurChemie
, Wien, 67 (1935), 598-609, is complex and usually results in low aldehyde yields.
３−フェノキシベンズアルデヒドおよびある種のその誘
導体が、容易に入手できる出発材料から高収量で容易に
得られるということが確認された。It has been determined that 3-phenoxybenzaldehyde and certain derivatives thereof are readily obtained in high yields from readily available starting materials.
従つて本発明は、３−ブロモベンズアルデヒドまたはそ
のアセタールを、中性有機溶媒の存在下かつ銅原子また
は銅イオンの存在下で、フェノールまたはそのアルカリ
金属塩と反応させることを特徴とする、３−フェノキシ
ベンズアルデヒドまたはそのアセタールの製造方法を提
供する。フェノールのアルカリ金属塩は、好ましくは、
ナトリウムまたはカリウムの塩であり、ナトリウム塩は
、３−フェノキシベンズアルデヒドに対しより高い選択
性を示すので特に好ましい。塩は、好ましくは、無水物
であり、その理由は、水の存在が、３−フェノキシベン
ズアルデヒドの収量を減するからである。無水塩は、フ
ェノールをアルカリ金属の水酸化物と反応させ、生成し
た水をトルエンまたはキシレンと共に共沸混合物として
除去することによつて製造され得る。別法として、フエ
ノールを、アルカリ金属アルコキシドと反応させ、生成
したアルカノールを蒸留によつて除去してもよい。中性
溶媒は、芳香族炭化水素たとえばトルエンまたはキシレ
ン；芳香族複素環系窒素化合物たとえばピリジン、２，
４，６−トリメチルピリジン、キノリンまたはピリジン
−Ｎ−オキシド；ジアルキルアミドたとえばジメチルホ
ルムアミドまたはジメチルアセトアミド；スルホキシド
たとえばジメチルスルホキシドまたはテトラヒドロチオ
フエン１，１−ジオキシドであつてよい。Therefore, the present invention is characterized in that 3-bromobenzaldehyde or its acetal is reacted with phenol or its alkali metal salt in the presence of a neutral organic solvent and in the presence of copper atoms or copper ions. Provided is a method for producing phenoxybenzaldehyde or its acetal. The alkali metal salt of phenol is preferably
Sodium or potassium salts are particularly preferred, with the sodium salt exhibiting higher selectivity for 3-phenoxybenzaldehyde. The salt is preferably anhydrous since the presence of water reduces the yield of 3-phenoxybenzaldehyde. Anhydrous salts may be prepared by reacting phenol with an alkali metal hydroxide and removing the resulting water as an azeotrope with toluene or xylene. Alternatively, the phenol may be reacted with an alkali metal alkoxide and the resulting alkanol removed by distillation. Neutral solvents include aromatic hydrocarbons such as toluene or xylene; aromatic heterocyclic nitrogen compounds such as pyridine, 2,
They may be 4,6-trimethylpyridine, quinoline or pyridine-N-oxide; dialkylamides such as dimethylformamide or dimethylacetamide; sulfoxides such as dimethylsulfoxide or tetrahydrothiophene 1,1-dioxide.
これら溶剤の混合物も使用できる。銅イオンに関しては
銅化合物が挙げられ、銅化合物は、銅（）化合物たとえ
ば弗化第二銅、塩化第二銅、酸化第二銅または銅（Ｐ−
クロロベンゾエート、または銅（１）化合物たとえば塩
化第一銅、臭化第一銅、沃化第一銅、酸化第一銅でよい
。Mixtures of these solvents can also be used. Regarding copper ions, mention may be made of copper compounds, which include copper () compounds such as cupric fluoride, cupric chloride, cupric oxide or copper (P-
It may be a chlorobenzoate, or a copper(1) compound such as cuprous chloride, cuprous bromide, cuprous iodide, cuprous oxide.
３−ブロモベンズアルデヒドおよびフエノールまたは塩
は、どのようなモル比で使用されてもよいが、好ましく
は、ベンズアルデヒド；（フエノールまたは塩）のモル
比は、０．５：１〜２：１特に０．９：１〜１．１：１
である。3-bromobenzaldehyde and phenol or salt may be used in any molar ratio, but preferably the molar ratio of benzaldehyde; (phenol or salt) is between 0.5:1 and 2:1, especially 0.5:1 to 2:1. 9:1~1.1:1
It is.
銅化合物の３−ブロモベンズアルデヒドに対するモル比
は、好ま．しくは、１：１００〜１０：１００である。
反応温度は、たとえば５０〜２００℃、好ましくは、１
００〜１５０℃、反応時間は、１〜５時間でよいＯアセ
タールは、好ましくは、エチレングリコールのような二
価アルコールから誘導される。The molar ratio of the copper compound to 3-bromobenzaldehyde is preferably . Preferably, it is 1:100 to 10:100.
The reaction temperature is, for example, 50 to 200°C, preferably 1
00-150°C, reaction time may be 1-5 hours. The O acetal is preferably derived from a dihydric alcohol such as ethylene glycol.
３−フエノキシベンズアルデヒドは、シアン化水素と反
応させてアルフアーシアノ一３−フエノキシベンジルア
ルコールを得るかまたは水素添加して３−フエノキシベ
ンジルアルコールを得ることができ、これらはピレトリ
ン一型殺虫剤のエステルの２つの先駆物質である。3-Phenoxybenzaldehyde can be reacted with hydrogen cyanide to obtain alpha cyano-3-phenoxybenzyl alcohol or hydrogenated to obtain 3-phenoxybenzyl alcohol, which are pyrethrin type 1 Two precursors of pesticide esters.
本発明をさらに例を参照して説明する。The invention will be further explained with reference to examples.
例１
乾燥カリウムフェノラード（０．０２モル）は、フエノ
ール（０．０２モル）と水酸化カリウム（０．０２モル
）とを反応させ、さらに生成した水をトルエンとの共沸
混合物として除去することにより得た。Example 1 Dry potassium phenolate (0.02 mol) is prepared by reacting phenol (0.02 mol) with potassium hydroxide (0.02 mol) and removing the water formed as an azeotrope with toluene. I got it by doing that.
フェノラード、３−ブロモベンズアルデヒド（０．０２
モル）、塩化第１銅（０．０００５モル）およびピリジ
ン（５ｍ０を還流下に２時間加熱した。この混合物をジ
エチルエーテル５０ｍ１に溶解させ、このエーテル溶液
を水で洗浄（３Ｘ５０１１１）してから無水硫酸ナトリ
ウムにより乾燥させた。ＧＬＣ分析によれば、３−ブロ
モベンズアルデヒドの９７％が変換され、３−フエノキ
シベンズアルデヒドへの選択性が８５％であることが確
認された。エーテル溶液を蒸発させ、残留物を蒸留して
、純粋な３−フエノキシベンズアルデヒド（０．８ｍｍ
Ｈ９での沸点１２５℃、収量７４％）が得られた。３−
フエノキシベンズアルデヒドは、ビスルフイド錯体によ
つても精製され得る。Phenolade, 3-bromobenzaldehyde (0.02
mol), cuprous chloride (0.0005 mol) and pyridine (5 m0) were heated under reflux for 2 hours. The mixture was dissolved in 50 ml of diethyl ether and the ether solution was washed with water (3X50111) before drying. Dried over sodium sulfate. GLC analysis confirmed 97% conversion of 3-bromobenzaldehyde with 85% selectivity to 3-phenoxybenzaldehyde. The ether solution was evaporated. , the residue was distilled to give pure 3-phenoxybenzaldehyde (0.8 mm
A boiling point of H9 of 125°C and a yield of 74% were obtained. 3-
Phenoxybenzaldehyde can also be purified by bisulfide complexes.
比較実１験 Ａ例１の手順を３−クロロベンズアルデヒ
ドを使用して繰り返した。Comparative Experiment 1 Experiment A The procedure of Example 1 was repeated using 3-chlorobenzaldehyde.
僅か約１０％の３−フエノキシベンズアルデヒドを含む
複雑な混合生成物が得られた。例
３−ブロモベンズアルデヒドエチレングリコールアセタ
ールを使用し、反応時間を５時間として例１の手順で行
なつた。A complex mixed product containing only about 10% of 3-phenoxybenzaldehyde was obtained. Example 3 - The procedure of Example 1 was followed using bromobenzaldehyde ethylene glycol acetal and a reaction time of 5 hours.
ＧＬＣ分析によれば、出発材料ｌこ対し９０％の転化率
で、３−フエノキシベンズアルデヒドエチレングリコー
ルアセタールへの選択性９２％であることが確認された
。比較例 Ｂ３−クロロベンズアルデヒドエチレングリ
コールアセタールを使用して例川と同様な手順で行なつ
た。GLC analysis confirmed a 92% selectivity to 3-phenoxybenzaldehyde ethylene glycol acetal at a conversion of 90% based on the starting material. Comparative Example B The same procedure as in the example was carried out using 3-chlorobenzaldehyde ethylene glycol acetal.
６時間後で、５％より低い転化率であつた。After 6 hours, the conversion was less than 5%.
例〜ピリジンの代りに他の３種類溶剤を使用して例Ｉの
手順で行なつた。Example - The procedure of Example I was followed using three other solvents in place of pyridine.
表１に使用溶剤、転化率および３−フエノキシベンズア
ルデヒドへの選択性を示してある。※ ４０ｍ１を使用
し、還流時間は３．５時間でぁつた。Table 1 shows the solvent used, the conversion rate and the selectivity to 3-phenoxybenzaldehyde. *40ml was used and the reflux time was 3.5 hours.
水酸化ナトリウム０．０５モルおよびフエノール０，０
５モルを、ｏ−、ｍ−およびｐ−キシレンの商業用混合
物７５ｍ１に混合した。Sodium hydroxide 0.05 mol and phenol 0.0
5 mol were mixed into 75 ml of a commercial mixture of o-, m- and p-xylene.
Claims (1)
を、中性有機溶媒の存在下かつ銅原子または銅イオンの
存在下で、フェノールまたはそのアルカリ金属塩と反応
させることを特徴とする、３−フェノキシベンズアルデ
ヒドまたはそのアセタールの製造方法。 ２ アルカリ金属塩が、ナトリウムまたはカリウムの塩
であることを特徴とする特許請求の範囲第１項に記載の
製造方法。 ３ 溶媒がピリジンであることを特徴とする特許請求の
範囲第１または２項に記載の製造方法。 ４ 銅イオンが、銅（ I ）化合物の銅イオンであるこ
とを特徴とする特許請求の範囲第１ないし３項のいずれ
かに記載の製造方法。 ５ ３−ブロモベンズアルデヒドのフェノールまたはそ
のアルカリ金属塩に対するモル比が０．５ないし２の範
囲であることを特徴とする特許請求の範囲第１ないし４
項のいずれかに記載の製造方法。 ６ 温度が５０℃ないし２００℃であることを特徴とす
る特許請求の範囲第１ないし５項のいずれかに記載の製
造方法。[Claims] 1 3-bromobenzaldehyde or its acetal is reacted with phenol or its alkali metal salt in the presence of a neutral organic solvent and a copper atom or copper ion. - A method for producing phenoxybenzaldehyde or its acetal. 2. The manufacturing method according to claim 1, wherein the alkali metal salt is a sodium or potassium salt. 3. The manufacturing method according to claim 1 or 2, wherein the solvent is pyridine. 4. The manufacturing method according to any one of claims 1 to 3, wherein the copper ion is a copper ion of a copper (I) compound. 5. Claims 1 to 4, characterized in that the molar ratio of 3-bromobenzaldehyde to phenol or its alkali metal salt is in the range of 0.5 to 2.
The manufacturing method described in any of paragraphs. 6. The manufacturing method according to any one of claims 1 to 5, wherein the temperature is 50°C to 200°C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23770/75A GB1539733A (en) | 1975-06-02 | 1975-06-02 | Preparation of 3-phenoxybenzaldehydes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51143638A JPS51143638A (en) | 1976-12-10 |
| JPS5944294B2 true JPS5944294B2 (en) | 1984-10-29 |
Family
ID=10201046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51062449A Expired JPS5944294B2 (en) | 1975-06-02 | 1976-05-31 | Method for producing 3-phenoxybenzaldehydes |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5944294B2 (en) |
| AR (1) | AR210130A1 (en) |
| AU (1) | AU500419B2 (en) |
| BE (1) | BE842177A (en) |
| BR (1) | BR7603435A (en) |
| CA (1) | CA1075246A (en) |
| CH (1) | CH601155A5 (en) |
| DD (1) | DD124378A5 (en) |
| DE (1) | DE2624360A1 (en) |
| DK (1) | DK238676A (en) |
| ES (1) | ES448384A1 (en) |
| FR (1) | FR2313340A1 (en) |
| GB (1) | GB1539733A (en) |
| HU (1) | HU173926B (en) |
| IE (1) | IE42827B1 (en) |
| IL (1) | IL49686A (en) |
| IT (1) | IT1060881B (en) |
| LU (1) | LU75055A1 (en) |
| NL (1) | NL7605830A (en) |
| NO (1) | NO761850L (en) |
| SE (1) | SE7606116L (en) |
| SU (1) | SU910113A3 (en) |
| TR (1) | TR19245A (en) |
| ZA (1) | ZA763220B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006155A1 (en) * | 1978-06-08 | 1980-01-09 | Ciba-Geigy Ag | 3-Phenoxybenzyl amines and 3-benzylbenzyl amines and process for their production |
| GB2185016B (en) * | 1985-12-20 | 1989-11-29 | Hardwicke Chemical Co | Process for preparing 3-phenoxybenzaldehydes |
| US4691033A (en) * | 1985-12-20 | 1987-09-01 | Hardwicke Chemical Company | Process for preparing 3-phenoxybenzaldehydes |
| EP3816155A1 (en) | 2013-08-23 | 2021-05-05 | Virginia Commonwealth University | Ester nitrates derivatives of aromatic aldehydes with multiple pharmalogic properties to treat sickle cell disease |
| FR3031977B1 (en) * | 2015-01-22 | 2018-04-20 | Centre National De La Recherche Scientifique | PROCESS FOR PRODUCING AN ABLATIVE RESIN |
| FR3031978B1 (en) | 2015-01-22 | 2018-04-20 | Centre National De La Recherche Scientifique | PROCESS FOR PRODUCING AN ABLATIVE RESIN |
| CN110256285B (en) * | 2019-07-09 | 2022-03-18 | 上海出入境检验检疫局动植物与食品检验检疫技术中心 | Synthetic method of stable isotope labeled pyrethroid |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR818032A (en) * | 1936-02-29 | 1937-09-16 | Geigy Ag J R | Process for the preparation of aldehydes of the series of diaryl or polyaryl ethers |
-
1975
- 1975-06-02 GB GB23770/75A patent/GB1539733A/en not_active Expired
-
1976
- 1976-04-28 CA CA251,331A patent/CA1075246A/en not_active Expired
- 1976-05-25 BE BE1007409A patent/BE842177A/en not_active IP Right Cessation
- 1976-05-31 JP JP51062449A patent/JPS5944294B2/en not_active Expired
- 1976-05-31 AR AR263460A patent/AR210130A1/en active
- 1976-05-31 LU LU75055A patent/LU75055A1/xx unknown
- 1976-05-31 SU SU762439451A patent/SU910113A3/en active
- 1976-05-31 DE DE19762624360 patent/DE2624360A1/en not_active Withdrawn
- 1976-05-31 CH CH680776A patent/CH601155A5/xx not_active IP Right Cessation
- 1976-05-31 IE IE1151/76A patent/IE42827B1/en unknown
- 1976-05-31 SE SE7606116A patent/SE7606116L/en unknown
- 1976-05-31 IT IT23800/76A patent/IT1060881B/en active
- 1976-05-31 IL IL49686A patent/IL49686A/en unknown
- 1976-05-31 AU AU14444/76A patent/AU500419B2/en not_active Expired
- 1976-05-31 NO NO761850A patent/NO761850L/no unknown
- 1976-05-31 FR FR7616352A patent/FR2313340A1/en active Granted
- 1976-05-31 NL NL7605830A patent/NL7605830A/en not_active Application Discontinuation
- 1976-05-31 BR BR7603435A patent/BR7603435A/en unknown
- 1976-05-31 DK DK238676A patent/DK238676A/en not_active Application Discontinuation
- 1976-05-31 DD DD193099A patent/DD124378A5/xx unknown
- 1976-05-31 TR TR19245A patent/TR19245A/en unknown
- 1976-05-31 ES ES448384A patent/ES448384A1/en not_active Expired
- 1976-06-01 ZA ZA763220A patent/ZA763220B/xx unknown
- 1976-06-02 HU HU76SE1837A patent/HU173926B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2624360A1 (en) | 1976-12-16 |
| GB1539733A (en) | 1979-01-31 |
| FR2313340B1 (en) | 1978-11-17 |
| IL49686A (en) | 1979-05-31 |
| CH601155A5 (en) | 1978-06-30 |
| BR7603435A (en) | 1977-02-15 |
| ES448384A1 (en) | 1977-08-01 |
| FR2313340A1 (en) | 1976-12-31 |
| AR210130A1 (en) | 1977-06-30 |
| SU910113A3 (en) | 1982-02-28 |
| CA1075246A (en) | 1980-04-08 |
| BE842177A (en) | 1976-11-25 |
| HU173926B (en) | 1979-09-28 |
| IL49686A0 (en) | 1976-07-30 |
| SE7606116L (en) | 1976-12-03 |
| AU500419B2 (en) | 1979-05-24 |
| LU75055A1 (en) | 1977-02-15 |
| JPS51143638A (en) | 1976-12-10 |
| NO761850L (en) | 1976-12-03 |
| DD124378A5 (en) | 1977-02-16 |
| NL7605830A (en) | 1976-12-06 |
| IT1060881B (en) | 1982-09-30 |
| IE42827L (en) | 1976-12-02 |
| ZA763220B (en) | 1977-05-25 |
| AU1444476A (en) | 1977-12-08 |
| DK238676A (en) | 1976-12-03 |
| TR19245A (en) | 1978-08-02 |
| IE42827B1 (en) | 1980-10-22 |
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