JPS6126975B2 - - Google Patents
Info
- Publication number
- JPS6126975B2 JPS6126975B2 JP55065771A JP6577180A JPS6126975B2 JP S6126975 B2 JPS6126975 B2 JP S6126975B2 JP 55065771 A JP55065771 A JP 55065771A JP 6577180 A JP6577180 A JP 6577180A JP S6126975 B2 JPS6126975 B2 JP S6126975B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- methyl
- group
- general formula
- naoh
- 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
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- -1 furancarbinol compound Chemical class 0.000 claims description 7
- BZKFMUIJRXWWQK-UHFFFAOYSA-N cyclopenten-2-one Natural products O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- HNNRFEWGWVQYNP-UHFFFAOYSA-N 4-hydroxy-4-methyl-5-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1(O)C=CC(=O)C1CC=C HNNRFEWGWVQYNP-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- NOWHXSQOXFHUPB-UHFFFAOYSA-N 1-(5-methylfuran-2-yl)but-3-yn-1-ol Chemical compound CC1=CC=C(C(O)CC#C)O1 NOWHXSQOXFHUPB-UHFFFAOYSA-N 0.000 description 1
- JHEKTJPJMNQKRA-UHFFFAOYSA-N 1-(5-methylfuran-2-yl)pentan-1-ol Chemical compound CCCCC(O)C1=CC=C(C)O1 JHEKTJPJMNQKRA-UHFFFAOYSA-N 0.000 description 1
- BLXRCUAXNAVKIQ-UHFFFAOYSA-N 4-hydroxy-4-methyl-5-prop-2-ynylcyclopent-2-en-1-one Chemical compound CC1(O)C=CC(=O)C1CC#C BLXRCUAXNAVKIQ-UHFFFAOYSA-N 0.000 description 1
- VSAISQPJOKIOJC-UHFFFAOYSA-N 5-butyl-4-hydroxy-4-methylcyclopent-2-en-1-one Chemical compound CCCCC1C(=O)C=CC1(C)O VSAISQPJOKIOJC-UHFFFAOYSA-N 0.000 description 1
- OUDFNZMQXZILJD-UHFFFAOYSA-N 5-methyl-2-furaldehyde Chemical compound CC1=CC=C(C=O)O1 OUDFNZMQXZILJD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は３−オキソシクロペンテン化合物の製
造方法に関し、さらに詳しくは一般式（）
〔式中、R1は炭素数６までのアルキル基、その結
合末端に不飽和結合を持たない炭素数６までのア
ルケニル基、アルキニル基または一般式
The present invention relates to a method for producing a 3-oxocyclopentene compound, and more particularly, to a method for producing a 3-oxocyclopentene compound, more specifically, a method for producing a 3-oxocyclopentene compound, and more specifically, [In the formula, R 1 is an alkyl group with up to 6 carbon atoms, an alkenyl group with up to 6 carbon atoms that does not have an unsaturated bond at the bond end, an alkynyl group, or a general formula
で示される化合物にMg、ZnまたはAl金属を作用
させて得られる一般式（）
R1MX （）
〔式中、R1およびＸは前述と同じ意味を有し、Ｍ
はMg、ZnまたはAl2/3原子を表わす。〕
で示される化合物を５−メチルフルフラールと反
応させることにより得ることができる。
以下、実施例により本発明を具体的に説明す
る。
実施例 １
水１と５−メチル−２−フリル−アリル−カ
ルビノール25ｇを仕込み、1N NaOHおよび1N
HCl水溶液でPHを5.5に調製した。これを100℃に
昇温し、還流させ1N NaOHおよび1N HCl水溶液
でPH5.0〜5.5に保つて12時間還流撹拌した。次に
40℃まで冷却後1N−NaOH水で中和後、食塩300
ｇを加えトルエン100mlで５回抽出した。抽出液
を60℃、減圧下にトルエンを留去し、23ｇの油状
物を得た。次にこれを0.1mmHg、77℃で蒸留して
21.3ｇの４−ハイドロオキシ−４−メチル−５−
アリル−２−シクロペンテノンを得た。収率85.2
％
NMRデータ（CCl4、内部標準TMS、δppm、
60MHz）
7.32（ｄ、1H、３−Ｈ）、5.92（ｄ、1H、２−
Ｈ）、
5.81（complex ｍ、1H、−CH2−ＣＨ＝
CHaHb）、
5.12（ｍ、1H、−CH2−CH＝ＣＨ aＨb）、
4.93（ｍ、1H、−CH2−CH＝CHa Ｈ b）、
4.12（broad Ｓ、1H、４−ＯＨ）
2.37（ｍ、3H、５−Ｈ＆−ＣＨ ２−CH＝
CHaHb）
1.28（Ｓ、3H、４−ＣＨ ３）
実施例 ２
水200mlと５−メチル−２−フリル−プロパル
ギル−カルビノール５ｇを仕込み、1N NaOHお
よび1N HCl水溶液でPHを４に調製した。これを
100℃に昇温し還流させ、1N NaOHおよび1N
HCl水溶液でPH3.8〜4.1に保つて16時間還流撹拌
した。
次に40℃まで冷却後、1N NaOH水で中和後、
食塩60ｇを加え、トルエン20mlで５回抽出した。
抽出液を60℃減圧下にトルエンを留去し、4.0ｇ
の油状物を得た。次にこれをシリカゲル60ｇを使
用して酢酸エチル／ｎ−ヘキサン（１容対２容）
で展開し、目的の４−ハイドロオキシ−４−メチ
ル−５−プロパルギル−２−シクロペンテノン
3.7ｇを得た。収率74％
NMRデータ（CDCl3内部標準TMS、δppm、
90MHz）
7.30（ｄ、1H、３−Ｈ）、5.90（ｄ、1H、２−
Ｈ）、
3.80（broad ｓ、1H、４−ＯＨ）
1.98（Ｓ、1H、−Ｃ≡ＣＨ）、1.30（ｓ、3H、
４−ＣＨ ３）
実施例 ３
水40mlと５−メチル−２−フリル−ｎ−ブチル
−カルビノール0.5ｇを仕込み、1N NaOHおよび
1N HCl水溶液でPHを５に調整した。これを100℃
に昇温し還流させ、1N NaOHおよび1N HCl水溶
液でPH５〜5.5に保つて30時間還流撹拌した。次
に40℃まで冷却後、1N NaOH水で中和後、食塩
12ｇを加え、トルエン40mlで５回抽出する。抽出
液を60℃減圧下にトルエンを留去し、0.48ｇの油
状物を得た。これをシリカゲル薄層クロマトグラ
フイーを使用して、酢酸エチル−ｎ−ヘキサン
（１容対２容）で展開した。
目的の分画をかきとり、酢酸エチルで溶出させ
シリカゲルをロ過後濃縮して、４−ハイドロオキ
シ−４−メチル−５−ｎ−ブチル−２−シクロペ
ンテノン3.5ｇを得た。収率70％
NMRデータ（CCl4内部標準TMS、δppm、
60MHz）
7.25（ｄ、1H、３−Ｈ）、5.85（ｄ、1H、２−
Ｈ）、
3.63（broad ｓ、1H、４−ＯＨ）
2.20（ｍ、1H、５−Ｈ）
1.25（Ｓ、3H、４−ＣＨ ３）
実施例 ４〜９
下記のフランカルビノール化合物0.5ｇを用
い、下記の条件で実施例３と同様の操作を行い
夫々の３−オキソシクロペンテン化合物を得た。
General formula () R 1 MX () obtained by reacting Mg, Zn or Al metal to the compound represented by
represents Mg, Zn or Al2/3 atoms. ] It can be obtained by reacting the compound represented by these with 5-methylfurfural. Hereinafter, the present invention will be specifically explained with reference to Examples. Example 1 Prepare 1 water and 25 g of 5-methyl-2-furyl-allyl-carbinol, add 1N NaOH and 1N
The pH was adjusted to 5.5 with aqueous HCl. This was heated to 100° C., refluxed, maintained at pH 5.0 to 5.5 with 1N NaOH and 1N HCl aqueous solution, and stirred under reflux for 12 hours. next
After cooling to 40℃ and neutralizing with 1N-NaOH water, add 300% salt.
g and extracted 5 times with 100 ml of toluene. Toluene was distilled off from the extract under reduced pressure at 60°C to obtain 23 g of oil. Next, this was distilled at 0.1 mmHg and 77℃.
21.3 g of 4-hydroxy-4-methyl-5-
Allyl-2-cyclopentenone was obtained. Yield 85.2
% NMR data ( CCl4 , internal standard TMS, δppm,
60MHz) 7.32 (d, 1H, 3-H), 5.92 (d, 1H, 2-
H), 5.81 (complex m, 1H, -CH2 - CH =
CH a H b ), 5.12 (m, 1H, -CH 2 -CH=CH a H b ), 4.93 (m, 1H, -CH 2 -CH=CH a H b ), 4.12 (broad S, 1H, 4- OH ) 2.37(m, 3H, 5-H& -CH2 - CH =
CH a H b ) 1.28 (S, 3H, 4- CH 3 ) Example 2 Prepare 200 ml of water and 5 g of 5-methyl-2-furyl-propargyl-carbinol, and adjust the pH to 4 with 1N NaOH and 1N HCl aqueous solution. Prepared. this
Heat to 100℃ and reflux, add 1N NaOH and 1N
The mixture was stirred under reflux for 16 hours while maintaining the pH at 3.8 to 4.1 with an aqueous HCl solution. Next, after cooling to 40℃ and neutralizing with 1N NaOH water,
60 g of common salt was added and extracted 5 times with 20 ml of toluene.
Toluene was distilled off from the extract under reduced pressure at 60℃, and 4.0g
of oil was obtained. Next, use 60 g of silica gel to prepare ethyl acetate/n-hexane (1 volume vs. 2 volumes).
to obtain the desired 4-hydroxy-4-methyl-5-propargyl-2-cyclopentenone.
3.7g was obtained. Yield 74% NMR data (CDCl 3 internal standard TMS, δppm,
90MHz) 7.30 (d, 1H, 3-H), 5.90 (d, 1H, 2-
H), 3.80 (broad s, 1H, 4- OH ) 1.98 (S, 1H, -C≡CH ) , 1.30 (s, 3H,
4- CH3 ) Example 3 40 ml of water and 0.5 g of 5-methyl-2-furyl-n-butyl - carbinol were added, and 1N NaOH and
The pH was adjusted to 5 with 1N HCl aqueous solution. This at 100℃
The temperature was raised to reflux, the pH was maintained at 5 to 5.5 with 1N NaOH and 1N HCl aqueous solution, and the mixture was stirred under reflux for 30 hours. Next, after cooling to 40℃ and neutralizing with 1N NaOH water, salt
Add 12g and extract 5 times with 40ml of toluene. Toluene was distilled off from the extract under reduced pressure at 60°C to obtain 0.48 g of oil. This was developed using silica gel thin layer chromatography with ethyl acetate-n-hexane (1 volume to 2 volumes). The desired fraction was scraped off, eluted with ethyl acetate, filtered through silica gel, and concentrated to obtain 3.5 g of 4-hydroxy-4-methyl-5-n-butyl-2-cyclopentenone. Yield 70% NMR data ( CCl4 internal standard TMS, δppm,
60MHz) 7.25 (d, 1H, 3-H), 5.85 (d, 1H, 2-
H), 3.63 (broad s, 1H, 4- OH ) 2.20 (m, 1H, 5-H) 1.25 (S, 3H, 4- CH ) Examples 4 to 9 0.5 g of the following furancarbinol compound The same operation as in Example 3 was performed using the following conditions under the following conditions to obtain each 3-oxocyclopentene compound.
【表】【table】
【表】
＊ 上記一般式〓および〓で示される化
合物のR１の内容
実施例 10
水750mlを仕込み、100℃に昇温し還流させる。
次に５−メチル−２−フリル−アリル−カルビ
ノール24ｇとMgCl2・6H2O31.5ｇを水160mlに溶
解した液を各々2.5時間と3.5時間を要し滴下し
た。その時反応液のPHが10％リン酸１カリ水溶液
と1N−水酸化ナトリウム水でPH5.7〜5.3の間にあ
るように制御した。
反応開始後1.5時間付近からPHは変化しなくな
つた。
MgCl2水溶液の滴下終了後、PH5.5の状態で4.5
時間、100℃で還流撹拌した。
これを40℃まで冷却後、1N水酸化ナトリウム
水で中和し、食塩320ｇを加えた後、トルエン250
mlで４回抽出した。抽出液を無水硫酸マグネシウ
ムで乾燥後、60℃減圧下にトルエンを留去したと
ころ21.6ｇの油状物を得た。
次にこれを0.5mmHg、88〜90℃で蒸留して20.4
ｇの４−ハイドロオキシ−４−メチル−５−アリ
ル−２−シクロペンテノンを得た。収率85％
実施例 11
水150ml、トリ−ｎ−オクチル−メチル−アン
モニウムクロライド450mgを仕込み、1/3Ｎ HCl
水溶液と1/3Ｎ NaOH水溶液でPH5.5に調製す
る。次に５−メチル−２−フリル−アリル−カル
ビノール11.0ｇを加え、100℃に昇温し、還流さ
せ、1/3Ｎ NaOH水溶液と1/3Ｎ HCl水溶液で
PH５〜5.5に保つて７時間還流撹拌した。次に40
℃まで冷却後、食塩30ｇを加え、トルエン70mlで
５回抽出する。60℃減圧下にトルエンを留去した
ところ10.1ｇの油状物を得た。次にこれをシリカ
ゲル100ｇを使用して酢酸エチル−ｎ−ヘキサン
（１容対２容）で展開し、目的の４−ハイドロオ
キシ−４−メチル−５−アリル−２−シクロペン
テノン7.1ｇを得た。収率64.5％[Table] * Contents Example 1 of R1 of the compound represented by the above general formulas 〓 and 〓 10 Charge 750 ml of water, heat to 100°C, and reflux. Next, a solution prepared by dissolving 24 g of 5-methyl-2-furyl-allyl-carbinol and 1.5 g of MgCl 2 .6H 2 O in 160 ml of water was added dropwise over 2.5 hours and 3.5 hours, respectively. At that time, the pH of the reaction solution was controlled to be between 5.7 and 5.3 using a 10% monopotassium phosphoric acid aqueous solution and 1N aqueous sodium hydroxide. The pH stopped changing around 1.5 hours after the start of the reaction. After dropping the MgCl 2 aqueous solution, the pH is 4.5 at 5.5.
The mixture was stirred under reflux at 100°C for an hour. After cooling this to 40℃, neutralize it with 1N sodium hydroxide solution, add 320g of table salt, and add 250g of toluene.
Extracted 4 times with ml. After drying the extract over anhydrous magnesium sulfate, toluene was distilled off under reduced pressure at 60°C to obtain 21.6 g of an oily substance. Next, this was distilled at 0.5 mmHg and 88 to 90℃ to obtain a 20.4
g of 4-hydroxy-4-methyl-5-allyl-2-cyclopentenone was obtained. Yield 85% Example 11 150 ml of water and 450 mg of tri-n-octyl-methyl-ammonium chloride were added, and 1/3N HCl
Adjust the pH to 5.5 with aqueous solution and 1/3N NaOH aqueous solution. Next, 11.0 g of 5-methyl-2-furyl-allyl-carbinol was added, the temperature was raised to 100°C, refluxed, and 1/3N NaOH aqueous solution and 1/3N HCl aqueous solution were added.
The mixture was stirred under reflux for 7 hours while maintaining the pH at 5 to 5.5. then 40
After cooling to ℃, add 30 g of common salt and extract 5 times with 70 ml of toluene. Toluene was distilled off at 60° C. under reduced pressure to obtain 10.1 g of oil. Next, this was developed using 100 g of silica gel with ethyl acetate-n-hexane (1 volume to 2 volumes) to obtain 7.1 g of the desired 4-hydroxy-4-methyl-5-allyl-2-cyclopentenone. Obtained. Yield 64.5%
Claims (1)
合末端に不飽和結合を持たない炭素数６までのア
ルケニル基、アルキニル基または一般式
【式】で示される基を表わす。 ここにR2は水素原子、メチル基またはハロゲン
原子を表わす。〕 で示されるフランカルビノール化合物を、水溶媒
中、触媒の存在下或いは非存在下に、PH３〜６、
20〜120℃で処理することを特徴とする一般式 〔式中、R1は前述と同じ意味を有する〕 で示される３−オキソシクロペンテン化合物の製
造方法。 ２ 触媒が金属塩および／または界面活性剤であ
る特許請求の範囲第１項に記載の製造方法。[Claims] 1. General formula [In the formula, R 1 represents an alkyl group having up to 6 carbon atoms, an alkenyl group having up to 6 carbon atoms, an alkynyl group, or a group represented by the general formula [Formula] having no unsaturated bond at the bond end. R 2 here represents a hydrogen atom, a methyl group or a halogen atom. ] The furancarbinol compound represented by is added in an aqueous solvent in the presence or absence of a catalyst at pH 3 to 6,
General formula characterized by processing at 20-120℃ [In the formula, R 1 has the same meaning as above] A method for producing a 3-oxocyclopentene compound represented by the following. 2. The manufacturing method according to claim 1, wherein the catalyst is a metal salt and/or a surfactant.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6577180A JPS56161344A (en) | 1980-05-16 | 1980-05-16 | Preparation of 3-oxocyclopentene compound |
| HU287680A HU186372B (en) | 1979-12-06 | 1980-12-03 | Process for producing 3-oxo-cyclopentene derivatives |
| DE8080107671T DE3063547D1 (en) | 1979-12-06 | 1980-12-05 | 3-hydroxy-4-cyclopentenones and process for their production |
| EP19800107671 EP0031909B1 (en) | 1979-12-06 | 1980-12-05 | 3-hydroxy-4-cyclopentenones and process for their production |
| DK522280A DK160294C (en) | 1979-12-06 | 1980-12-05 | METHOD OF PREPARING 3-OXYCYCLOPENTENES |
| US06/213,632 US4356326A (en) | 1979-12-06 | 1980-12-05 | Process for producing 3-oxocyclopentenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6577180A JPS56161344A (en) | 1980-05-16 | 1980-05-16 | Preparation of 3-oxocyclopentene compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56161344A JPS56161344A (en) | 1981-12-11 |
| JPS6126975B2 true JPS6126975B2 (en) | 1986-06-23 |
Family
ID=13296615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6577180A Granted JPS56161344A (en) | 1979-12-06 | 1980-05-16 | Preparation of 3-oxocyclopentene compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56161344A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010761A1 (en) * | 1978-11-01 | 1980-05-14 | Sumitomo Chemical Company, Limited | Process for preparing 4-hydroxy-2-cyclopenten-I-ones, 2-methyl-2,5-dimethoxy-2,5-dihydrofurans and a process for their preparation |
-
1980
- 1980-05-16 JP JP6577180A patent/JPS56161344A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010761A1 (en) * | 1978-11-01 | 1980-05-14 | Sumitomo Chemical Company, Limited | Process for preparing 4-hydroxy-2-cyclopenten-I-ones, 2-methyl-2,5-dimethoxy-2,5-dihydrofurans and a process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56161344A (en) | 1981-12-11 |
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