JPS60258138A - Preparation of 4-hydroxycyclopentenone - Google Patents
Preparation of 4-hydroxycyclopentenoneInfo
- Publication number
- JPS60258138A JPS60258138A JP59116253A JP11625384A JPS60258138A JP S60258138 A JPS60258138 A JP S60258138A JP 59116253 A JP59116253 A JP 59116253A JP 11625384 A JP11625384 A JP 11625384A JP S60258138 A JPS60258138 A JP S60258138A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- cyclobentenone
- acetoxy
- methyl
- reaction
- 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.)
- Granted
Links
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)
Abstract
Description
【発明の詳細な説明】
本発明は、一般式（１）
（式中、Ｒ１は水素原子、アルキル基またはアルテニル
基を、Ｒ２はアルキル基、アルテニル基またはアラレキ
ニル基をそれぞれ示す。）で示される４−ヒドロキシシ
クロベンテノン類の製造法に関し、更に詳しくは、一般
式（Ｉ）（式中、Ｒ′は水素原子または低級アルキル基
である。Ｒ３およびＲ２は前記と同じ意味を有する。）
で示されるｄ／−４−シクロベンテノン類（以下、単に
４−シクロベンテノン類と呼ぶ）を、水および酸性物質
の共存下に反応させることからなる前記一般式（１）で
示される４−ヒドロキシシクロベンテノン類の製造法で
ある。DETAILED DESCRIPTION OF THE INVENTION The present invention is represented by the general formula (1) (wherein R1 represents a hydrogen atom, an alkyl group, or an artenyl group, and R2 represents an alkyl group, an artenyl group, or an aralekynyl group, respectively). Regarding the method for producing 4-hydroxycyclobentenones, more specifically, the general formula (I) (wherein R' is a hydrogen atom or a lower alkyl group. R3 and R2 have the same meanings as above) d/-4-cyclobentenones (hereinafter simply referred to as 4-cyclobentenones) shown in the formula (1) are reacted in the presence of water and an acidic substance. This is a method for producing hydroxycyclobentenones.
本発明により得られる一般式（１）で示される４−ヒド
ロキシシクロベンテノン類は農薬あるいは医薬中間体と
しＣ重要であるばかりでなく、香料あるいはその中間体
とし°Ｃ有用な化合物である。とくに、菊酸のエステル
に導き、ピレスロイド系殺虫剤として用いられるため、
農薬用中間体とし′Ｃ重要な化合物である。The 4-hydroxycyclobentenones represented by the general formula (1) obtained by the present invention are not only important as agricultural chemicals or pharmaceutical intermediates, but are also useful compounds as fragrances or intermediates thereof. In particular, it is converted into an ester of chrysanthemum acid and is used as a pyrethroid insecticide.
It is an important compound as an intermediate for agricultural chemicals.
従来、かかる一般式（１）で示される４−ヒドロキシシ
クロベンテノン類の合成法としては、数多くの方法が知
られているが、高価な原料を使う、収率が悪い等工業的
な製法としては決して満足のいくものではなかった。Many methods have been known for synthesizing 4-hydroxycyclobentenones represented by the general formula (1), but there are many industrial methods that use expensive raw materials and poor yields. was never satisfactory.
このような状況下で、本発明者らは前記一般式（１）で
示される４−ヒドロキシシクロベンテノンの製造法につ
いて研究した結果、従来全く知られていない経路でかつ
高純度、高収率で目的物を得、しかも工業的に有利な方
法を見い出した。Under these circumstances, the present inventors conducted research on a method for producing 4-hydroxycyclobentenone represented by the general formula (1), and found that it was possible to produce 4-hydroxycyclobentenone using a previously unknown route with high purity and high yield. We have found a method that allows us to obtain the desired product and is also industrially advantageous.
すなわち本発明は、前記一般式（１）で示される４−シ
クロベンテノン類を水および酸性物質の共存下に反応さ
せることにより、一般式（１）で示される４−ヒドロキ
シシクロベンテノン類を得る方法である。That is, the present invention provides 4-hydroxycyclobentenones represented by the general formula (1) by reacting the 4-cyclobentenones represented by the general formula (1) in the presence of water and an acidic substance. This is the way to get it.
尚、本発明に類似するものとし゛Ｃ，Ｃクシクロベンテ
ノン類位反応に関して
１７４４（１９８２）
に記載の方法が知られている。しかしこれらはいずれも
エステルからエステーレへの転位であり、工業的にも満
足のいく方法ではなく、農薬としても使用オ６え□２１
よ、。ｉｎ １７７１９体。カ。 □１水分解を実施し
なければならず、この加水分解の収率も決して満足のい
くものではなかった。Incidentally, as a method similar to the present invention, a method described in 1744 (1982) regarding the C,C cyclobentenone group reaction is known. However, these are all rearrangements from ester to estere, and these are not industrially satisfactory methods, and they are also used as pesticides.
Yo,. in 17719 bodies. mosquito. □1 Hydrolysis had to be carried out, and the yield of this hydrolysis was by no means satisfactory.
しかるに、本発明者らが見い出した方法は４−シクロベ
ンテノン類から一気に４−ヒドロキシシクロベンテノン
類を得るものであり、従来全く知られていない新規な方
法であるばかりでなく、収率、純度の点で極めてすぐれ
たものであり・工業的利用価値は計り知れないものがあ
る。However, the method discovered by the present inventors obtains 4-hydroxycyclobentenones from 4-cyclobentenones at once, and is not only a novel method that has not been previously known, but also improves the yield and It has extremely high purity and its industrial value is immeasurable.
以下に本発明の詳細な説明する。The present invention will be explained in detail below.
本発明において、原料として用いられる４−シクロベン
テノン類としては、たとえば８−アセトキシ−２−メチ
ル−４−シクロベンテノン、８−アセトキシ−２−エチ
ル−４−シクロベンテノン、８−アセトキシ−２−ｎ−
プロピル−４−シクロベンテノン、８−アセトキシ−２
−イツープロビ１１／−４−シクロベンテノン、８−ア
セトキシ−２−ｎ−ブチル−１９’４−シクロベンテノ
ン、８−アセトキシ−２−ｎ−ペンチル−４−シクロベ
ンテノン、８−アセトキシ−２−ｎ−へキシル−４−シ
クロベンテノン、８−アセトキシ−２−ｎ−へブチ！レ
ー４−シクロベンテノン、８−アセトキシ−２−アリデ
レー４−シクロベンテノン、８−アセトキシ−２−（２
−シスーブテニ＋ｐ ） −４−シクロベンテノン、８
−アセトキシ−２−（ω−ブテニル）−４−シクロベン
テノン、８−アセトキシ−２−（２−）ランスーペンテ
ニ＋ｌｙ ）−４−シクロベンテノン、８−アセトキシ
−２−（８−シス−ヘキセニル）−４−シクロベンテノ
ン、８−アセトキシ−２−プロパルギル−４−シクロベ
ンテノン、８−アセトキシ−２−（２−ペンチニル）−
４−シクロベンテノン、８−アセトキシ−２−（α−メ
チルアリル）−４−シクロベンテノン、８−アセトキシ
−２−（１−シクロペ ′ンテニル）−４−シクロベン
テノン、８−アセトキシ−２−シクロへキシル−４−シ
クロベンテノン、８−アセトキシ−２，８−ジメチル−
４−シクロベンテノン、３−アセトキシ−２−エチ１１
／−８−メチルー４−シクロベンテノン、８−アセトキ
シ−２−ｎ−プロピル−３−メチルー４−シクロベンテ
ノン、８−アセトキシ−２−イソプロピル−８−メチク
レー４−シクロベンテノン、８−アセトキシ−２−ｎ−
ブチシレー８−メチ−シー４−シクロベンテノン、８−
アセトキシ−２−ｎ−ペンチル−８−メチＩＬ＋−４−
シクロベンテノン、８−アセトキシ−２−ｎ−ヘキシ＋
１７−１３−メチル−４−シクロベンテノン、８−アセ
トキシ−２−ｎ−へブチル−８−メチル−４−シクロベ
ンテノン、８−アセトキシ−２−アリル−８−メチル−
４−シクロベンテノン、８−アセトキシ−２−（２−シ
スーブテニやし）−３−メチル−４−シクロベンテノン
、８−アセトキシ−２−（ω−ブテニル）−８−メチル
−４−シクロベンテノン、８−アセトキシ−２−（２−
シス−ペンテニル）−８−メチル−４−シクロベンテノ
ン、８−アセトキシ−２−Ａ２−）ランスーペンテニ＋
１／） −８−メチル−４−シクロベンテノン、８−ア
セトキシ−２−（８−シス−ヘキセニル）−８−メチル
−４−シクロベンテノン、８−アセトキシ−２−プロパ
ルキＩＬ／ −７３−メチル−４−シクロベンテノン、
８−アセトキシ−２−（２−ペンチニル）−８−メチル
−４−シクロベンテノン、８−アセドキシー２−（α−
メチルアリ・し）−８−メチ「レー４−シクロベンテノ
ン、８−アセトキシ−２−（ｌ−シクロベンテノンレ）
−８−メチシレー４−シクロベンテノン、８−アセトキ
シ−２−シクロヘキシ＋１／−９−メチル−４−シクロ
ベンテノンおよびこれらの化合物における８−位のアセ
トキシ基がプロピオニルオキシ基、ホｔレミル基、ブテ
ノイルオキシ基などのアシルオキシル基に置換された化
合物が例示される。In the present invention, the 4-cyclobentenones used as raw materials include, for example, 8-acetoxy-2-methyl-4-cyclobentenone, 8-acetoxy-2-ethyl-4-cyclobentenone, and 8-acetoxy-2-ethyl-4-cyclobentenone. 2-n-
Propyl-4-cyclobentenone, 8-acetoxy-2
-Itsuprobi11/-4-cyclobentenone, 8-acetoxy-2-n-butyl-19'4-cyclobentenone, 8-acetoxy-2-n-pentyl-4-cyclobentenone, 8-acetoxy-2 -n-hexyl-4-cyclobentenone, 8-acetoxy-2-n-hebuty! 4-cyclobentenone, 8-acetoxy-2-alideley 4-cyclobentenone, 8-acetoxy-2-(2
-cis-buteni+p) -4-cyclobentenone, 8
-acetoxy-2-(ω-butenyl)-4-cyclobentenone, 8-acetoxy-2-(2-)lansupentenyl)-4-cyclobentenone, 8-acetoxy-2-(8-cis-hexenyl) -4-cyclobentenone, 8-acetoxy-2-propargyl-4-cyclobentenone, 8-acetoxy-2-(2-pentynyl)-
4-cyclobentenone, 8-acetoxy-2-(α-methylallyl)-4-cyclobentenone, 8-acetoxy-2-(1-cyclopentenyl)-4-cyclobentenone, 8-acetoxy-2- Cyclohexyl-4-cyclobentenone, 8-acetoxy-2,8-dimethyl-
4-cyclobentenone, 3-acetoxy-2-ethyl 11
/-8-methyl-4-cyclobentenone, 8-acetoxy-2-n-propyl-3-methyl-4-cyclobentenone, 8-acetoxy-2-isopropyl-8-methiclay-4-cyclobentenone, 8-acetoxy -2-n-
butycyle 8-methy-cy-4-cyclobentenone, 8-
Acetoxy-2-n-pentyl-8-methyL+-4-
Cyclobentenone, 8-acetoxy-2-n-hexy+
17-13-Methyl-4-cyclobentenone, 8-acetoxy-2-n-hebutyl-8-methyl-4-cyclobentenone, 8-acetoxy-2-allyl-8-methyl-
4-Cyclobentenone, 8-acetoxy-2-(2-cis-butenyl)-3-methyl-4-cyclobentenone, 8-acetoxy-2-(ω-butenyl)-8-methyl-4-cyclobenten Non, 8-acetoxy-2-(2-
cis-pentenyl)-8-methyl-4-cyclobentenone, 8-acetoxy-2-A2-)lansupentenyl+
1/) -8-Methyl-4-cyclobentenone, 8-acetoxy-2-(8-cis-hexenyl)-8-methyl-4-cyclobentenone, 8-acetoxy-2-propalkIL/ -73- Methyl-4-cyclobentenone,
8-acetoxy-2-(2-pentynyl)-8-methyl-4-cyclobentenone, 8-acetoxy-2-(α-
4-cyclobentenone, 8-acetoxy-2-(l-cyclobentenone)
-8-Methysyle 4-cyclobentenone, 8-acetoxy-2-cyclohexy+1/-9-methyl-4-cyclobentenone, and in these compounds, the acetoxy group at the 8-position is a propionyloxy group, a photoremyl group, Examples include compounds substituted with an acyloxyl group such as a butenoyloxy group.
この反応で用いられる酸性物質としＣは塩酸、硫酸、硝
酸、リン酸、塩素酸、ポリリン酸、ホウ酸、トルエンス
セホン酸、メタンスルホン酸、酢酸等の通常の無機酸、
有機酸が例示され、その使用量は原料である一般式（Ｉ
）で示され−る４−、ヶ。／＜：、ｔｆ／□、、、ヵｔ
、”ｃ’ｏ、ｔ〜ｉ ｏ ｏ＠エ ）・□？し、好まし
くは０．５〜５０倍モルの範囲である。The acidic substances used in this reaction C are ordinary inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, chloric acid, polyphosphoric acid, boric acid, toluenesefonic acid, methanesulfonic acid, acetic acid, etc.
Organic acids are exemplified, and the amount used is based on the general formula (I
) 4-, month. /<:, tf/□,,,cat
, "c'o, t~io@e)・□?", preferably in the range of 0.5 to 50 times the mole.
また、水の使用量は原料４−シクロベンテノン類に対し
て一般的には等モル以上であるが、酸性物質として有機
力・レボン酸を用いる場合は８倍モル以上、特に５倍モ
ル以上であることが好ましい。上限に′ついては何ら制
限的でないが一般には２０モｔし倍である。In addition, the amount of water used is generally at least equimolar to the raw material 4-cyclobentenone, but when organic acid/levonic acid is used as the acidic substance, it is at least 8 times the mole, especially at least 5 times the mole. It is preferable that There is no restriction on the upper limit, but it is generally 20 times higher.
この反応において、上記水は溶媒とし“Ｃも利用するこ
とができ、その他必要に応じてテトラヒドロフラン、ジ
オキサン、アセトン、ベンゼン、トルエン、ジメチルス
ルホキシド、ジメチルホルムアミド、ヘキサン、ジエチ
ルエーテ１し、ジクロルメタン、クロロホルム等の脂肪
族もしくは芳香族炭化水素、エーテル、ｒトン、ハロゲ
ン化炭化水素などの反応に不活性な溶媒の単独または混
合物を溶媒とし′Ｃ用いることができる。In this reaction, water can be used as a solvent, and other substances such as tetrahydrofuran, dioxane, acetone, benzene, toluene, dimethyl sulfoxide, dimethylformamide, hexane, diethyl ether, dichloromethane, chloroform, etc. can be used as necessary. A single or a mixture of solvents inert to the reaction, such as aliphatic or aromatic hydrocarbons, ethers, r-tons, and halogenated hydrocarbons, can be used as the solvent.
反応温度は一１０〜１８０℃の範囲で任意であるが、好
ましくはθ℃〜１１０℃の範囲である。The reaction temperature is arbitrary in the range of -10 to 180°C, but preferably in the range of θ°C to 110°C.
反応時間については特に制限はない。There is no particular restriction on the reaction time.
このような反応によっＣ１一般式（１）で示される４−
ヒドロキシシクロベンテノン類が容易に、かつ好収率で
得られ、これらは通常の分離手段、たとえば抽出、分液
、濃縮、蒸留等により反応混合物から容易に単離するこ
とができる。Through such a reaction, 4- represented by C1 general formula (1)
Hydroxycyclobentenones are easily obtained in good yields and can be easily isolated from the reaction mixture by conventional separation means such as extraction, separation, concentration, distillation, etc.
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
攪拌装置、温度計を装着した四ツ目フラスコに２０％硫
酸１０ｍ１を仕込み、内温を８０〜５０℃に調節しなか
らｄｔ −８−アセトキシ−２−アリル−８−メチル−
４−シクロベンテノン２ｇを１時間にて加える。滴下終
了後、同温度にて８時間保温する。Example 1 10 ml of 20% sulfuric acid was charged into a four-eye flask equipped with a stirrer and a thermometer, the internal temperature was adjusted to 80 to 50°C, and then dt-8-acetoxy-2-allyl-8-methyl-
Add 2 g of 4-cyclobentenone over 1 hour. After finishing dropping, keep warm at the same temperature for 8 hours.
反応終了後、食塩８ｆを加え、メチルイソブチルデトン
２０ｍ１に゛Ｃ８回抽出する。有機層は、飽和食塩水に
て水洗いしたのちメチルイソブチルゲトンを留去する。After the reaction was completed, 8 f of common salt was added, and the mixture was extracted 8 times with 20 ml of methyl isobutyl detone. The organic layer is washed with saturated brine, and then methyl isobutyl getone is distilled off.
濃縮残渣をカラムクロマト精製して２−アリ９レー４−
ヒドロキシ−８−メチＩＬＬ−２−シクロベンテノン１
．２７ｇ（収率８４％）を得た。The concentrated residue was purified by column chromatography to obtain 2-aryl 4-
Hydroxy-8-methyILL-2-cyclobentenone 1
．． 27 g (yield 84%) was obtained.
尚、上記実施例において、２０％硫酸１０ｍｌの代わり
に表−１に示す酸性物質の水溶液１０ｍ＋／を用いる以
外は全く同様に反応させ、処理した結果、目的化合物の
収率は表−１に示すとおりであった。In addition, in the above example, the yield of the target compound as a result of the reaction and treatment was as shown in Table 1. That's right.
表−１
実施例２
実施例１で用いたと同様のフラスコに８−アセトキシ−
２−ｎ−ペンチル−８−メチル−４−シクロベンテノン
２．２４ｇ、テトラヒドロフラン（ＴＨＦ）１（１＋ｌ
および２０％硫酸１０ｖｔｌを仕込み、８０〜５０℃に
て６時間攪拌する。Table 1 Example 2 8-acetoxy-
2.24 g of 2-n-pentyl-8-methyl-4-cyclobentenone, 1 (1+l) of tetrahydrofuran (THF)
and 10 vtl of 20% sulfuric acid, and stirred at 80 to 50°C for 6 hours.
反応終了後、実施例１に準じて後処理、精製しＣ４−ヒ
ドロキシ−２−ｎ−ペンチル８−メチル−２−シクロベ
ンテノン（収率１．５５８５％）を得た。After the reaction was completed, the product was post-treated and purified according to Example 1 to obtain C4-hydroxy-2-n-pentyl 8-methyl-2-cyclobentenone (yield: 1.5585%).
実施例８
３−アセトキシ−２−アリル−８−メチツレ−４−シク
ロベンテノンに代え′で８−アセトキシ−２−アリル−
４−シクロベンテノン１．８ｆを使用する以外は実施例
１と同様に反応、後処理し、さらにカラムクロマト精製
（トルエン：酢酸エチル−５二４）して２−アリＶレー
４−ヒドロキシー２−シクロベンテノン１．１５Ｆ（収
率８８．５％）を得た。Example 8 In place of 3-acetoxy-2-allyl-8-methyl-4-cyclobentenone, 8-acetoxy-2-allyl-
The reaction and post-treatment were carried out in the same manner as in Example 1, except that 1.8f of 4-cyclobentenone was used, and further column chromatography purification (toluene:ethyl acetate-524) was carried out to obtain 2-aryl V-ray 4-hydroxy-2. -Cyclobentenone 1.15F (yield 88.5%) was obtained.
実施例４
８−アセトキシ−２−アリル−８−メチル−４−シクロ
ベンテノンに代えて２−アリル−８−プロピオニワレオ
キシ−８−メチル−４−シクロベンテノン２．０８ｆを
使用する以外は実施例１と同様に反応、後処理、精製し
Ｃ２−アリル−４−ヒドロキシ８−メチル−２，１，。Example 4 Except for using 2.08f of 2-allyl-8-propioniwareoxy-8-methyl-4-cyclobentenone in place of 8-acetoxy-2-allyl-8-methyl-4-cyclobentenone. was reacted, worked up and purified in the same manner as in Example 1 to obtain C2-allyl-4-hydroxy-8-methyl-2,1.
−シクロベンテノン１．２６ｇ（８８％）を得た。- 1.26 g (88%) of cyclobentenone were obtained.
実施例５
実施例１で用いたと同様のフラスコに１０％塩酸水１（
１＋／およびジオキサンＬＯ＋ｌを仕込み、内温４０〜
５０℃にて２−アリ９レー８−アセトキシ−８−メチ１
１／−４−シクロベンテノン１．９４ｇを２時間にて加
える。その後同温度で８時間攪拌する。Example 5 In a flask similar to that used in Example 1, add 1 part of 10% hydrochloric acid (
1+/ and dioxane LO+l, and the internal temperature is 40~
2-aryl9re8-acetoxy-8-methy1 at 50°C
Add 1.94 g of 1/-4-cyclobentenone over 2 hours. Thereafter, the mixture was stirred at the same temperature for 8 hours.
以下、実施例１に準じて後処理し、２−アリル−８−メ
チル−４−ヒドロキシ−２−シクロベンテノン１．２８
ｇ（収率８４．５％）を得た。Hereinafter, post-treatment was carried out according to Example 1, and 2-allyl-8-methyl-4-hydroxy-2-cyclobentenone 1.28
g (yield: 84.5%).
また、ジオキサンに代えてテトラヒドロフランを用いて
同様に行ったところ目的物１．２９ｇ（収率８５％）を
得た。Moreover, when the same procedure was carried out using tetrahydrofuran instead of dioxane, 1.29 g (yield: 85%) of the target product was obtained.
実施例６〜９
４−シクロベンテノン類として、表２に示す化合物を用
い、表−２に示す条件以外は実施例１と同様に反応させ
、処理した結果を表−２に示す。Examples 6 to 9 Using the compounds shown in Table 2 as 4-cyclobentenones, the reaction was carried out in the same manner as in Example 1 except for the conditions shown in Table 2. The results of the treatment are shown in Table 2.
実施例Ｉ
実施例１で用いたと同様の装置に８−アセトキシ−２−
アリル−８−メチル−４−シクロベンテノンｓ、ｏｙ、
水１ｏｙおよヒ酢Ｍ ５ｇを仕込み、還流下に、１０時
間攪拌する。Example I In a device similar to that used in Example 1, 8-acetoxy-2-
Allyl-8-methyl-4-cyclobentenone s,oy,
Add 1 oy of water and 5 g of arsenic vinegar M, and stir under reflux for 10 hours.
反応終了後、反応液を減圧下に濃縮し、メチＩレイソブ
チ％ ｆ ）ン６０ｔｔｔｌに゛ｃ３回抽出する。After the reaction is completed, the reaction solution is concentrated under reduced pressure and extracted three times with 60 tttl of methyl lyobutylene (%f).
抽出有機層をあわせ、水洗ののち、硫酸マグネシウムに
゛Ｃ乾燥する。The extracted organic layers were combined, washed with water, and then dried over magnesium sulfate (C).
有機層を減圧濃縮し、さらにカラムクロマトグラフィー
にで精製しｃ１２− アリル−４−ヒドロキシ−８−メ
チル−２−シクロペンチノン１．９５１収率８３％）を
得た。The organic layer was concentrated under reduced pressure and further purified by column chromatography to obtain c12-allyl-4-hydroxy-8-methyl-2-cyclopentyone (1.951 yield, 83%).
Claims (1)
は水素原子、アルキル基またはアルテニｌｌ’Ｍヲ、Ｒ
２はアルキ−レ基、アルケニル基マたはアルキニル基を
それぞれ示す。） で示されるｄｉ −４−シクロベンテノン類を、水およ
び酸性物質の共存下に反応させることを特徴とする一般
式 （式中、Ｒ，およびＲ２は前記と同じ意味を有する。） で示される４−ヒドロキシシクロベンテノン類の製造法
。[Claims] General formula (wherein R' is a hydrogen atom or a lower alkyl group, R3
is a hydrogen atom, an alkyl group, or an alkyl group, R
2 represents an alkylene group, an alkenyl group, or an alkynyl group, respectively. ) represented by the general formula (wherein R and R2 have the same meanings as above), characterized by reacting di-4-cyclobentenones represented by A method for producing 4-hydroxycyclobentenones.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59116253A JPS60258138A (en) | 1984-06-05 | 1984-06-05 | Preparation of 4-hydroxycyclopentenone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59116253A JPS60258138A (en) | 1984-06-05 | 1984-06-05 | Preparation of 4-hydroxycyclopentenone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60258138A true JPS60258138A (en) | 1985-12-20 |
| JPH0556327B2 JPH0556327B2 (en) | 1993-08-19 |
Family
ID=14682545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59116253A Granted JPS60258138A (en) | 1984-06-05 | 1984-06-05 | Preparation of 4-hydroxycyclopentenone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60258138A (en) |
-
1984
- 1984-06-05 JP JP59116253A patent/JPS60258138A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0556327B2 (en) | 1993-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Miyashita et al. | A New and Efficient Esterification Reaction via Mixed Anhydrides by the Promotion of a Catalytic Amount of Lewis Acid. | |
| US4353829A (en) | Process for 5-aroylation of 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic esters | |
| JPS60258138A (en) | Preparation of 4-hydroxycyclopentenone | |
| EP0119091B1 (en) | 2,2-diethoxypropionic acid derivatives | |
| KR20030017473A (en) | One-pot synthesis of alkyl 3-cyclopropylamino-2-[2,4-dibromo-3-(difluoromethoxy)benzoyl]-2-propenoate as a useful intermediate for antibacterial quinolone medicaments | |
| JPH05140060A (en) | Production of 3-substituted amino-4,4,4-trifluorocrotonic acid ester | |
| US5516926A (en) | (+) 2-benzoyl-3-(silyloxyprop-2(S)-yl)aminoacrylate derivatives and a method for preparing the same | |
| JPH05279345A (en) | Production of 4,6-dialkoxypyrimidine | |
| JPH115756A (en) | Production of 2-alkyl azulene | |
| JPS63211264A (en) | Production of indolines | |
| Kim et al. | 2-benzoyl-3-(silyloxyprop-2 (S)-yl) aminoacrylate derivatives and a method for preparing the same | |
| JPH0269469A (en) | Dihydrofuran derivative and production thereof | |
| JPS61293979A (en) | Production of 3-substituted-2-formylthiophene compound | |
| Shved et al. | Reactions of silyl nitronates with dimethylformamide dimethyl acetal as a new general procedure for the synthesis of 2-nitroenamines | |
| JPH07133271A (en) | Banzaldehyde derivative and production of chromancarboxylic acid derivative using the same as intermediate | |
| JPH0812658A (en) | Production of sydnones | |
| JPH0586044A (en) | Method for producing beta-lactone and macrocyclic ketone | |
| JPS606951B2 (en) | Lactone production method | |
| JPH01272559A (en) | 2,6-diethylaniline derivative and production thereof | |
| JPS60181049A (en) | Production of chrysanthemic acid derivative | |
| JPH0253782A (en) | Production of formylaminothiazoleacetic acid derivative | |
| JPS63156754A (en) | Production of methyl 4-oxo-5-tetradecynoate | |
| JPH03145482A (en) | Production of optically active hydroxylactones | |
| JPH0699402B2 (en) | 4,4-Dibromo-1,3-dimethyl-2-pyrazolin-5-one and method for producing the same | |
| JPS61109771A (en) | Pyrazole derivative and its preparation |