JPH03856B2 - - Google Patents
Info
- Publication number
- JPH03856B2 JPH03856B2 JP57153369A JP15336982A JPH03856B2 JP H03856 B2 JPH03856 B2 JP H03856B2 JP 57153369 A JP57153369 A JP 57153369A JP 15336982 A JP15336982 A JP 15336982A JP H03856 B2 JPH03856 B2 JP H03856B2
- Authority
- JP
- Japan
- Prior art keywords
- dihalogeno
- reaction
- phenylpropionaldehyde
- phenylpropionic acid
- yield
- 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
- -1 azo compound Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 21
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ICNABEJOLUCNMJ-UHFFFAOYSA-N 2,3-dichloro-3-phenylpropanal Chemical compound O=CC(Cl)C(Cl)C1=CC=CC=C1 ICNABEJOLUCNMJ-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- WWPINMUWXRWOSY-UHFFFAOYSA-N 2,3-dichloro-3-phenylpropanoyl chloride Chemical compound ClC(=O)C(Cl)C(Cl)C1=CC=CC=C1 WWPINMUWXRWOSY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010813 internal standard method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000012493 hydrazine sulfate Substances 0.000 description 1
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明は２，３−ジハロゲノ−３−フエニルプ
ロピオン酸ハライドの製造方法に関する。
２，３−ジハロゲノ−３−フエニルプロピオン
酸ハライド自体は公知の化合物であり、このもの
は主に農薬製造の中間体として有用である。
従来２，３−ジハロゲノ−３−フエニルプロピ
オン酸ハライドの製造方法としては下記（）式
で表わされるように
（但し式中Ｘはハロゲン原子である。）
２，３−ジハロゲノ−３−フエニルプロピオン
アルデヒドを光照射下にハロゲン化する光化学反
応による方法〔ドポビデイ アカデミ ナウタ
ウクラインスコイ RSRキイン シリーズＢ
1975巻No.４ 344〜346頁（1975）；Dopovidi
Akademij Nauk Ukrains'koi RSR.Kijn Ser.
Bvol.1975 No.４ P.344〜346（1975）〕が知られ
ている。しかしながらこの方法は(1)光化学反応で
あるので装置が複雑かつ高価であること、(2)光源
の電力費によりコスト高となること、(3)光源が高
電圧のため危険性が高いこと及び(4)２，３−ジハ
ロゲノ−３−フエニルプロピオンアルデヒドから
の収率が75重量％以下という低収率であることな
ど全体として工業的に有利な方法とはいえない欠
点があつた。
本発明者等は上記に鑑み２，３−ジハロゲノ−
３−フエニルプロピオン酸ハライドの工業的に有
利な製造方法について種々研究した結果、前述の
（）の反応をアゾ化合物の存在下で行うと、工
業的に高収率で目的物が得られることを見出し本
発明を完成した。
即ち本発明は、２，３−ジハロゲノ−３−フエ
ニルプロピオンアルデヒドをハロゲン化して２，
３−ジハロゲノ−３−フエニルプロピオン酸ハラ
イドを製造する方法において、一般式
［式中Ｒ，R′は低級アルキル基又はシクロア
ルキル基であり、Ａはシアノ基、アルコキシカル
ボニル基を示す。］で表されるアゾ化合物を、２，
３−ジハロゲノ−３−フエニルプロピオンアルデ
ヒド１モルに対して50〜500mg存在させることを
特徴とする一般式
［式中Ｘはハロゲン原子を示す。］で表される
２，３−ジハロゲノ−３−フエニルプロピオン酸
ハライドの製造方法である。 本発明に使用する
ハロゲン化剤としては塩素、臭素等が一般的であ
る。
存在させるアゾ化合物の具体例としては
等の一種又は二種以上を挙げることができる。就
中α，α′−アゾビスイソブチロニトリルが好適で
ある。
これらのアゾ化合物は市販品を用いても良い
し、硫酸ヒドラジン、シアン化アルカリ、ケトン
からヒドラゾ化合物を得た後酸化すれば、収率よ
く得られるものである。これは２，３−ジハロゲ
ノ−３−フエニルプロピオンアルデヒドをハロゲ
ン化する際にラジカルを遊離し触媒機能を発揮す
る。
本発明は以上の原料を用いて反応を遂行するの
であるがその実施の態様を説明すると、まず２，
３−ジハロゲノ−３−フエニルプロピオンアルデ
ヒドを不活性有機溶媒、特にハロゲン化炭化水素
に混合し、次いでアゾ化合物を存在させ、更にハ
ロゲンを徐々に加えて反応を完了する。
この際使用できる不活性有機溶媒としては四塩
化炭素、クロロホルム、２塩化エタン、トリクロ
ロエチレン、テトラクロロエチレン、メチルクロ
ロホルム、モノクロルベンゼン等を挙げることが
でき、この内特に四塩化炭素が好ましい。その使
用量については特に限定されないが通常ハロゲン
導入、撹拌条件、温度条件、触媒の均一存在等に
支障のない範囲の量を用い、そのためには２，３
−ジハロゲノ−３−フエニルプロピオンアルデヒ
ドに対して２〜５倍容量も使用すれば良い。
存在させるアゾ化合物の量としては、２，３−
ジハロゲノ−３−フエニルプロピオンアルデヒド
１モルに対して50〜500mgで充分であり、好まし
くは100〜200mgである。50mg未満では目的物の収
率が充分でなく500mgを越えると目的物の収率が
下がるだけでなく
The present invention relates to a method for producing 2,3-dihalogeno-3-phenylpropionic acid halide. 2,3-dihalogeno-3-phenylpropionic acid halide itself is a known compound, and is mainly useful as an intermediate in the production of agricultural chemicals. The conventional method for producing 2,3-dihalogeno-3-phenylpropionic acid halide is as expressed by the following formula (). (However, in the formula, X is a halogen atom.) A photochemical reaction method in which 2,3-dihalogeno-3-phenylpropionaldehyde is halogenated under light irradiation [Dopovidei Academy Nauta]
Ukraineskoy RSR Kiin Series B
Volume 1975, No. 4, pages 344-346 (1975); Dopovidi
Akademij Nauk Ukrains'koi RSR.Kijn Ser.
Bvol.1975 No.4 P.344-346 (1975)] is known. However, this method requires (1) complicated and expensive equipment because it is a photochemical reaction, (2) high cost due to the electricity cost of the light source, and (3) high risk due to the high voltage of the light source. (4) The method had drawbacks such as a low yield of 75% by weight or less from 2,3-dihalogeno-3-phenylpropionaldehyde, which made it not an industrially advantageous method overall. In view of the above, the present inventors have determined that 2,3-dihalogen
As a result of various studies on industrially advantageous production methods for 3-phenylpropionic acid halide, it was found that the desired product can be obtained industrially in high yield when the above reaction () is carried out in the presence of an azo compound. They found this and completed the present invention. That is, the present invention provides 2,3-dihalogeno-3-phenylpropionaldehyde by halogenating it.
In the method for producing 3-dihalogeno-3-phenylpropionic acid halide, the general formula [In the formula, R and R' are a lower alkyl group or a cycloalkyl group, and A represents a cyano group or an alkoxycarbonyl group. ], an azo compound represented by 2,
General formula characterized by the presence of 50 to 500 mg per mole of 3-dihalogeno-3-phenylpropionaldehyde [In the formula, X represents a halogen atom. ] This is a method for producing 2,3-dihalogeno-3-phenylpropionic acid halide. Chlorine, bromine, etc. are commonly used as halogenating agents in the present invention. Specific examples of azo compounds to be present include One or more of these can be mentioned. Among these, α,α'-azobisisobutyronitrile is preferred. These azo compounds may be commercially available, or they can be obtained in good yield by obtaining the hydrazo compound from hydrazine sulfate, alkali cyanide, or ketone and then oxidizing it. This releases radicals and exhibits a catalytic function when halogenating 2,3-dihalogeno-3-phenylpropionaldehyde. The present invention carries out the reaction using the above-mentioned raw materials, and to explain its implementation mode, first 2.
The 3-dihalogeno-3-phenylpropionaldehyde is mixed in an inert organic solvent, especially a halogenated hydrocarbon, then the azo compound is present, and further halogen is gradually added to complete the reaction. Examples of inert organic solvents that can be used in this case include carbon tetrachloride, chloroform, ethane dichloride, trichloroethylene, tetrachloroethylene, methylchloroform, and monochlorobenzene, among which carbon tetrachloride is particularly preferred. The amount used is not particularly limited, but it is usually used within a range that does not interfere with halogen introduction, stirring conditions, temperature conditions, uniform presence of catalyst, etc.
-Dihalogeno-3-phenylpropionaldehyde may be used in an amount 2 to 5 times as large. The amount of the azo compound to be present is 2,3-
50 to 500 mg is sufficient, preferably 100 to 200 mg, per mole of dihalogeno-3-phenylpropionaldehyde. If it is less than 50 mg, the yield of the target product is insufficient, and if it exceeds 500 mg, not only will the yield of the target product decrease.
【式】に代
表される不純物の量が増加し好ましくない。この
量的関係は第１図から明らかである。即ち第１図
はα，α′−アゾビスイソブチロニトリルの添加量
に対して目的物である２，３−ジクロル−３−フ
エニルプロピオン酸クロライドの収率（％）及び
不純物（The amount of impurities represented by [Formula] increases, which is undesirable. This quantitative relationship is clear from FIG. That is, Figure 1 shows the yield (%) of the target product 2,3-dichloro-3-phenylpropionic acid chloride and the impurities (
【式】）の量をブ
ロツトしたグラフであり、アゾ化合物の量が２，
３−ジハロゲノ−３−フエニルプロピオンアルデ
ヒド１モルに対して50〜500mgの範囲外では目的
物の収率が低下しかつ不純物が増加することが分
かる。
次にハロゲンを導入し徐々に反応を進行させる
のであるが、その際のハロゲン使用量は２，３−
ジハロゲノ−３−フエニルプロピオンアルデヒド
に対して当モル量か、副生ハロゲン化水素に随伴
して消費される分を考慮してやや過剰に用いれば
充分である。
又反応温度については30〜80℃が適当で好まし
くは40〜60℃である。何んとなれば30℃未満では
反応の開始が遅くなり、80℃より高温になると副
生成物が増加して収率低下を招き好ましくないか
らである。尚上記温度範囲内で反応当初は高温域
で反応を開始させ、その後低温域で反応を続ける
ことは可能で収率低下は起こらない。通常反応当
初は反応速度が遅いが、アゾ化合物のラジカルが
連鎖的に生成するにつれて速くなる。
反応時間については、反応容量、溶媒の種類、
量、触媒、温度その他の操業条件によつて一様で
はないが通常２〜６時間も反応させれば充分であ
る。
反応終了後は常法に従つて溶媒を回収し、目的
物を得る。かくして本発明によれば一般的な反応
装置でしかも経済的、安全につまり工業的に高収
率で目的物を得ることが出来る。収率の一例を挙
げれば本発明により２，３−ジハロゲノ−３−フ
エニルプロピオン酸ハライドを製造すると２，３
−ジハロゲノ−３−フエニルプロピオンアルデヒ
ドを基準にした収率は94％以上になる。尚、２，
３−ジハロゲノ−３−フエニルプロピオン酸ハラ
イドの定量は、２，３−ジハロゲノ−３−フエニ
ルプロピオン酸ハライドをメチルエステル化した
ものをガスクロマトグラフ内部標準法により定量
したものである。
以下実施例を挙げて本発明を具体的に説明す
る。
実施例 １
還流冷却器、温度計、塩素吹き込み管及び撹拌
装置を具備した四つ口フラスコに２，３−ジクロ
ル−３−フエニルプロピオンアルデヒド101.5ｇ
（0.50モル）と四塩化炭素175ｇ及びα，α′−アゾ
ビスイソブチロニトリル50mgを加え、塩素を徐々
に導入しながら、60℃まで昇温した。約２時間経
過後から反応が速くなり４時間経過後の塩素を全
量で42.5ｇ（0.60モル）導入した時に反応は終了
した。
この反応液の一部を取り出し、メチルエステル
化し、ガスクロマトグラフ内部標準法により定量
した結果、メチルエステルとしての収率は94.5％
であつた。
実施例 ２
実施例１と同様の装置を備えた四つ口フラスコ
に２，３−ジクロル−３−フエニルプロピオンア
ルデヒド101.5ｇ（0.50モル）、四塩化炭素175ｇ、
及びα，α′−アゾビスイソブチロニトリル50mgを
仕込み、塩素を徐々に導入しながら、温度を60℃
に昇温した。約２時間後、反応が急速になつた
後、45℃に下げ反応を続けた。塩素を全量で42.5
ｇ（0.60モル）導入したとき反応が終了した。実
施例１と同様に定量した結果、メチルエステルと
しての収率は95.5％であつた。
比較例
実施例１と同様な装置を備えた四つ口フラスコ
に２，３−ジクロル−３−フエニルプロピオンア
ルデヒド101.5ｇ（0.50モル）及び四塩化炭素175
ｇを仕込んだ。次いで塩素42.5ｇを４時間かけて
導入した。しかしながら、その反応液をガスクロ
マトグラフで定量した結果２，３−ジクロル−３
−フエニルプロピオン酸クロライドは得られなか
つた。This is a graph blotting the amount of [Formula]), and the amount of azo compound is 2,
It can be seen that when the amount is outside the range of 50 to 500 mg per mole of 3-dihalogeno-3-phenylpropionaldehyde, the yield of the target product decreases and impurities increase. Next, halogen is introduced and the reaction proceeds gradually, but the amount of halogen used is 2,3-
It is sufficient to use it in an equimolar amount relative to dihalogeno-3-phenylpropionaldehyde, or in a slight excess in consideration of the amount consumed along with by-product hydrogen halide. The reaction temperature is suitably 30 to 80°C, preferably 40 to 60°C. This is because if the temperature is lower than 30°C, the start of the reaction will be delayed, and if the temperature is higher than 80°C, by-products will increase and the yield will decrease, which is undesirable. Note that within the above temperature range, it is possible to start the reaction at a high temperature range at the beginning of the reaction and then continue the reaction at a low temperature range without causing a decrease in yield. The reaction rate is usually slow at the beginning of the reaction, but becomes faster as the radicals of the azo compound are produced in a chain. Regarding reaction time, reaction volume, type of solvent,
Although it varies depending on the amount, catalyst, temperature and other operating conditions, it is usually sufficient to react for 2 to 6 hours. After the reaction is completed, the solvent is recovered according to a conventional method to obtain the desired product. Thus, according to the present invention, the desired product can be obtained economically and safely, that is, in industrially high yields, using a general reaction apparatus. To give an example of the yield, when 2,3-dihalogeno-3-phenylpropionic acid halide is produced according to the present invention, 2,3
The yield is 94% or more based on -dihalogeno-3-phenylpropionaldehyde. Furthermore, 2,
The quantification of 3-dihalogeno-3-phenylpropionic acid halide was determined by methyl esterification of 2,3-dihalogeno-3-phenylpropionic acid halide by gas chromatography internal standard method. The present invention will be specifically explained below with reference to Examples. Example 1 101.5 g of 2,3-dichloro-3-phenylpropionaldehyde was placed in a four-necked flask equipped with a reflux condenser, a thermometer, a chlorine injection tube, and a stirring device.
(0.50 mol), 175 g of carbon tetrachloride, and 50 mg of α,α'-azobisisobutyronitrile were added, and the temperature was raised to 60°C while gradually introducing chlorine. After about 2 hours, the reaction became faster, and the reaction was completed when 42.5 g (0.60 mol) of chlorine was introduced after 4 hours. A portion of this reaction solution was taken out, converted into methyl ester, and determined by gas chromatography internal standard method. As a result, the yield as methyl ester was 94.5%.
It was hot. Example 2 In a four-necked flask equipped with the same equipment as in Example 1, 101.5 g (0.50 mol) of 2,3-dichloro-3-phenylpropionaldehyde, 175 g of carbon tetrachloride,
and α, α′-azobisisobutyronitrile (50 mg), and while gradually introducing chlorine, the temperature was raised to 60°C.
The temperature rose to . After about 2 hours, the reaction became rapid, and then the temperature was lowered to 45°C and the reaction was continued. Total amount of chlorine is 42.5
g (0.60 mol) was introduced, the reaction was complete. As a result of quantitative determination in the same manner as in Example 1, the yield as methyl ester was 95.5%. Comparative Example In a four-neck flask equipped with the same equipment as in Example 1, 101.5 g (0.50 mol) of 2,3-dichloro-3-phenylpropionaldehyde and 175 carbon tetrachloride were added.
I prepared g. Then 42.5 g of chlorine was introduced over a period of 4 hours. However, when the reaction solution was quantitatively determined using a gas chromatograph, 2,3-dichloro-3
-Phenylpropionic acid chloride was not obtained.
第１図はα，α′−アゾビスイソブチロニトリル
の添加量に対して目的物の収率（％）及び不純物
の量をプロツトしたグラフである。
FIG. 1 is a graph plotting the yield (%) of the target product and the amount of impurities against the amount of α,α'-azobisisobutyronitrile added.
Claims (1)
ンアルデヒドをハロゲン化して２，３−ジハロゲ
ノ−３−フエニルプロピオン酸ハライドを製造す
る方法において、一般式 ［式中Ｒ，R′は低級アルキル基又はシクロア
ルキル基であり、Ａはシアノ基、アルコキシカル
ボニル基を示す。］で表されるアゾ化合物を、２，
３−ジハロゲノ−３−フエニルプロピオンアルデ
ヒド１モルに対して50〜500mg存在させることを
特徴とする一般式 ［式中Ｘはハロゲン原子を示す。］で表される
２，３−ジハロゲノ−３−フエニルプロピオン酸
ハライドの製造方法。[Scope of Claims] 1. A method for producing 2,3-dihalogeno-3-phenylpropionic acid halide by halogenating 2,3-dihalogeno-3-phenylpropionaldehyde, wherein the general formula [In the formula, R and R' are a lower alkyl group or a cycloalkyl group, and A represents a cyano group or an alkoxycarbonyl group. ], an azo compound represented by 2,
General formula characterized by the presence of 50 to 500 mg per mole of 3-dihalogeno-3-phenylpropionaldehyde [In the formula, X represents a halogen atom. ] A method for producing 2,3-dihalogeno-3-phenylpropionic acid halide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57153369A JPS5944339A (en) | 1982-09-04 | 1982-09-04 | Preparation of 2,3-dihalogeno-3-phenylpropionic acid halide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57153369A JPS5944339A (en) | 1982-09-04 | 1982-09-04 | Preparation of 2,3-dihalogeno-3-phenylpropionic acid halide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5944339A JPS5944339A (en) | 1984-03-12 |
| JPH03856B2 true JPH03856B2 (en) | 1991-01-09 |
Family
ID=15560943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57153369A Granted JPS5944339A (en) | 1982-09-04 | 1982-09-04 | Preparation of 2,3-dihalogeno-3-phenylpropionic acid halide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5944339A (en) |
-
1982
- 1982-09-04 JP JP57153369A patent/JPS5944339A/en active Granted
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS=1975 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5944339A (en) | 1984-03-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2928982B2 (en) | Method for producing 4'-bromomethyl-2-cyanobiphenyl | |
| JP2000319209A (en) | Production of iodinated aromatic compound | |
| JPH03856B2 (en) | ||
| JP3918883B2 (en) | Method for producing benzoyl chlorides | |
| EP0077853A1 (en) | Novel trifluoromethyl benzal chlorides and process for the preparation thereof | |
| KR940000060B1 (en) | Process of synthesis of acylcyanamides | |
| JP3788482B2 (en) | Method for producing alkylbenzoyl chloride | |
| JP3783733B2 (en) | Method for producing alkylbenzoyl chloride | |
| JP3882855B2 (en) | Method for producing alkylbenzoyl chloride | |
| JPH0827054A (en) | Bromination of aromatic compound | |
| JP2002167342A (en) | Method of producing adamantanediols | |
| JP2859791B2 (en) | Method for producing 4-bromomethylbiphenyl compound | |
| JP2556357B2 (en) | Method for producing 3,5-di-tert-butyl-2,6-dichlorotoluene | |
| JPH0686414B2 (en) | Method for producing acyl cyanide in anhydrous solvent | |
| JPH0656739A (en) | Production of 2,3-dihalogeno-3-phenylpropionic halide | |
| JP3164284B2 (en) | Method for producing 2-chloro-4-trifluoromethylbenzal chloride | |
| US3963751A (en) | Chlorination of butadiene sulfone to 3,3,4,4-tetrachlorotetrahydrothiophene-1,1-dioxide | |
| JPH05125017A (en) | Production of chloromethyl pivalate | |
| JPH05988A (en) | Production of trifluoroanisole compounds | |
| JPH05132446A (en) | Preparation of beta-halogeno-tert-alkylcarboxy- lic acid chlorides | |
| JP2001089422A (en) | Production of 2-chloro-4-nitroalkylbenzene | |
| JPS6330292B2 (en) | ||
| JPS6314693B2 (en) | ||
| JPS60116660A (en) | Manufacture of alpha-ketonitrile | |
| JPS63211242A (en) | Production of carbinol derivative |