JPH058176B2 - - Google Patents
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- Publication number
- JPH058176B2 JPH058176B2 JP59011408A JP1140884A JPH058176B2 JP H058176 B2 JPH058176 B2 JP H058176B2 JP 59011408 A JP59011408 A JP 59011408A JP 1140884 A JP1140884 A JP 1140884A JP H058176 B2 JPH058176 B2 JP H058176B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- atom
- group
- water
- general formula
- 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
- 150000003997 cyclic ketones Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000005979 thermal decomposition reaction Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- -1 1-methylthio-1-(p-tolylsulfonyl) Cyclohexane Chemical compound 0.000 description 2
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QLWXZRVOHCYKKK-UHFFFAOYSA-N n-(cyclohexylideneamino)-2,4-dinitroaniline Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1NN=C1CCCCC1 QLWXZRVOHCYKKK-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction 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
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明は、環状ケトン類の製造法に関する。さ
らに詳しくは、本発明は、一般式〔１〕
〔式中、Ａは
The present invention relates to a method for producing cyclic ketones. More specifically, the present invention relates to general formula [1] [In the formula, A is
【式】（Ｒは水素原
子、低級アルキル基、アルコキシ基またはハロゲ
ン原子を示す）を、Ｘは酸素原子、硫黄原子また
はメチレン基を、ｍおよびｎは整数を示す〕
で表されるメチルチオメチルアリールスルホン
誘導体を極性溶媒中水の存在下に加熱分解するこ
とを特徴とする一般式〔２〕
〔式中、Ｘは酸素原子、硫黄原子またはメチレ
ン基を、ｍおよびｎは整数を示す〕
で表される環状ケトン類の製造法に関する。
一般式〔２〕で表される環状ケトン類は工業薬
品、溶剤、医薬、農薬等として有用なものが多
く、また、これらの合成中間体として重要であ
る。
従来、一般式〔１〕で表されるメチルチオメチ
ルアリールスルホン誘導体より一般式〔２〕で表
される環状ケトン類を製造する方法としては酸性
条件下の方法が各種知られていた（特願昭58−
38630号公報およびChem.Lett.，1983，767〜
770）が、中性あるいは塩基性条件下の方法は知
られていなかつた。これまでの酸性条件下の方法
においても環状ケトン類は収率よく得られるが、
メチルチオ基およびアリールスルホニル基から誘
導される多種の化合物が副生し、所望環状ケトン
類の分離に煩雑な操作が要求される。本発明者は
この問題を解決すべく鋭意研究を重ねた結果、意
外にも極性溶媒中水の存在下加熱することにより
環状ケトン類が得られること、およびこの分解反
応が塩基を共存させても容易に進行することを見
いだし、本発明を完成した。
以下に本発明の製造法を詳細に説明するが、本
発明はこれらによつて限定されるものではない。
本発明における一般式〔１〕
で表されるメチルチオメチルアリールスルホン
誘導体の、Ａとしてはフエニル基、ｐ−トリル
基、ｐ−メトキシフエニル基、ｐ−クロロフエニ
ル基などのMethylthiomethylaryl represented by [Formula] (R represents a hydrogen atom, a lower alkyl group, an alkoxy group, or a halogen atom), X represents an oxygen atom, a sulfur atom, or a methylene group, and m and n represent integers] General formula [2] characterized by thermally decomposing a sulfone derivative in the presence of water in a polar solvent [In the formula, X represents an oxygen atom, a sulfur atom, or a methylene group, and m and n represent integers.] The present invention relates to a method for producing a cyclic ketone represented by the following formula. Many of the cyclic ketones represented by the general formula [2] are useful as industrial chemicals, solvents, medicines, agricultural chemicals, etc., and are also important as intermediates for their synthesis. Conventionally, various methods under acidic conditions have been known as methods for producing cyclic ketones represented by the general formula [2] from methylthiomethylarylsulfone derivatives represented by the general formula [1] (Japanese Patent Application No. 58−
Publication No. 38630 and Chem.Lett., 1983 , 767~
770), but no method under neutral or basic conditions was known. Although cyclic ketones can be obtained in good yield using conventional methods under acidic conditions,
Various compounds derived from the methylthio group and the arylsulfonyl group are produced as by-products, and complicated operations are required to separate the desired cyclic ketones. As a result of extensive research to solve this problem, the inventors of the present invention have surprisingly discovered that cyclic ketones can be obtained by heating in the presence of water in a polar solvent, and that this decomposition reaction can be carried out even in the presence of a base. They found that the process can be easily carried out and completed the present invention. The manufacturing method of the present invention will be explained in detail below, but the present invention is not limited thereto. General formula [1] in the present invention In the methylthiomethylarylsulfone derivative represented by, A is a phenyl group, p-tolyl group, p-methoxyphenyl group, p-chlorophenyl group, etc.
【式】（Ｒは水素原子、低
級アルキル基、アルコキシ基またはハロゲン原子
を示す）で表される基があげられる。
−（CH2）mX（CH2）ｎ−としては
−（CH2）2Ｏ（CH2）2−，−（CH2）5−，
−（CH2）3−などがあげられる。これらの化合物
は対応するメチルチオメチルアリールスルホン誘
導体から特願昭58−38630号公報の方法によつて
容易に合成できる。
加熱、分解は通常、水−メタノール、水−ジオ
キサン、水−エチレングリコールなどの極性溶媒
を用い、必要に応じて塩基、たとえば水酸化ナト
リウム、水酸化カリウム炭酸水素ナトリウム、リ
ン酸一水素ナトリウム等を共存させる。
加熱は50℃ないし反応液の還流温度まで行わ
れ、１時間ないし10日間で完結する。通常は高温
ほど、また塩基濃度が高いほど促進される傾向に
ある。
以上述べた条件によつて環状ケトン類が得られ
るが、本発明の方法は特別な酸性物質を必要とし
ない点で経済性および操作性に優れている。さら
に、塩基性物質を共存させる条件下ではアリール
スルホニル基から誘導されるアレンスルフイン酸
（ASO2Ｈ）がその塩として捕捉されるので、環
状ケトン類との分離が極めて容易になるととも
に、その塩はメチルチオメチルアリールスルホン
の原料として再使用が可能である。以上のように
本発明の方法は環状ケトン類の製造法として極め
て経済的なものといえる。
次に実施例をあげて本発明をさらに具体的に説
明するが本発明はこれらによつて限定されるもの
ではない。
実施例 １
１−メチルチオ−１−（ｐ−トリルスルホニル）
シクロヘキサノン126mgをエチレングリコール1.8
mlにとかし、水0.2mlおよび炭酸水素ナトリウム
113mgを加え90℃で６時間攪拌した。生成したシ
クロヘキサノンを捕捉するため２，４−ジニトロ
フエニルヒドラジン溶液（110mg／濃硫酸0.5ml＋
水0.75ml＋95％エタノール0.5ml）を加え、室温
で10分間攪拌した。これを水200mlに移し、ジク
ロロメタンで抽出したのち、有機層を無水硫酸マ
グネシウムで乾燥した。減圧濃縮したのちカラム
クロマトグラフイー（シリカゲル、ヘキサンとベ
ンゼンで留出）で分離して、シクロヘキサノン
２，４−ジニトロフエニルヒドラゾン109mgを橙
色結晶として得た。収率88％。同定は標品との混
融およびNMRの比較によつた。
実施例 ２〜６
１−メチルチオ−１−（ｐ−トリルスルホニル）
シクロヘキサンを実施例１と同様にして、種々の
条件で反応させ、生成したシクロヘキサノンを
２，４−ジニトロフエニルヒドラゾンに導いて定
量した。条件および結果を第１表に示す。Examples include groups represented by the formula: (R represents a hydrogen atom, a lower alkyl group, an alkoxy group, or a halogen atom). -( CH2 )mX( CH2 )n- includes -( CH2 ) 2O ( CH2 ) 2- , -( CH2 ) 5- , -( CH2 ) 3- , and the like. These compounds can be easily synthesized from the corresponding methylthiomethylarylsulfone derivatives by the method disclosed in Japanese Patent Application No. 58-38630. For heating and decomposition, a polar solvent such as water-methanol, water-dioxane, water-ethylene glycol, etc. is usually used, and if necessary, a base such as sodium hydroxide, potassium hydroxide, sodium bicarbonate, sodium monohydrogen phosphate, etc. is used. Let them coexist. Heating is performed from 50°C to the reflux temperature of the reaction solution, and is completed in 1 hour to 10 days. Usually, the higher the temperature and the higher the base concentration, the more accelerated the reaction will be. Although cyclic ketones can be obtained under the conditions described above, the method of the present invention is excellent in economy and operability in that no special acidic substance is required. Furthermore, under conditions in which a basic substance coexists, arenesulfinic acid (ASO 2 H) derived from an arylsulfonyl group is captured as its salt, making it extremely easy to separate it from cyclic ketones, and The salt can be reused as a raw material for methylthiomethylarylsulfone. As described above, the method of the present invention can be said to be extremely economical as a method for producing cyclic ketones. EXAMPLES Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto. Example 1 1-methylthio-1-(p-tolylsulfonyl)
Cyclohexanone 126mg to ethylene glycol 1.8
ml, 0.2ml water and sodium bicarbonate
113 mg was added and stirred at 90°C for 6 hours. 2,4-dinitrophenylhydrazine solution (110 mg/concentrated sulfuric acid 0.5 ml +
0.75 ml of water + 0.5 ml of 95% ethanol) was added, and the mixture was stirred at room temperature for 10 minutes. This was transferred to 200 ml of water, extracted with dichloromethane, and then the organic layer was dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was separated by column chromatography (silica gel, distilled with hexane and benzene) to obtain 109 mg of cyclohexanone 2,4-dinitrophenylhydrazone as orange crystals. Yield 88%. Identification was based on mixing with standard specimens and NMR comparison. Examples 2-6 1-methylthio-1-(p-tolylsulfonyl)
Cyclohexane was reacted under various conditions in the same manner as in Example 1, and the produced cyclohexanone was converted into 2,4-dinitrophenylhydrazone and quantified. The conditions and results are shown in Table 1.
【表】
実施例 ７
４−メチルチオ−４−（ｐ−トリルスルホニル）
テトラヒドロピラン112mgをメタノール50mlにと
かし、水１mlおよび炭酸水素ナトリウム205mgを
加え60℃で72時間攪拌した。以下実施例１と同様
にして生成したテトラヒドロ−４−ピロンを２，
４−ジニトロフエニルヒドラジンによつて捕捉し
テトラヒドロー４−ピロンの２，４−ジニトロフ
エニルヒドラゾン85.2mgを得た。収率82％。
融点191.5〜192.5℃（文献値＊186.5〜187℃）
＊Chem.Abstr.，49，8315b（1955）
実施例 ８
１−メチルチオ−１−（ｐ−トリルスルホニル）
シクロブタン102mgをエチレングリコール2.7mlに
とかし、水0.3mlおよび炭酸水素ナトリウム97mg
を加え90℃で７時間攪拌した。以下実施例１と同
様にして生成したシクロブタノンを２，４−ジニ
トロフエニルヒドラジンによつて捕捉しシリカゲ
ルカラムクロマトグラフイー分離によつて、シク
ロブタノン２，４−ジニトロフエニルヒドラゾン
89.4mgを得た。収率82％。
融点146.5〜148.0℃（文献値＊146℃）
＊Chem.Ber.，55，2737（1922）[Table] Example 7 4-methylthio-4-(p-tolylsulfonyl)
112 mg of tetrahydropyran was dissolved in 50 ml of methanol, 1 ml of water and 205 mg of sodium bicarbonate were added, and the mixture was stirred at 60°C for 72 hours. Below, tetrahydro-4-pyrone produced in the same manner as in Example 1 was added to 2,
Scavenging with 4-dinitrophenylhydrazine gave 85.2 mg of 2,4-dinitrophenylhydrazone of tetrahydro-4-pyrone. Yield 82%. Melting point 191.5-192.5°C (literature value *186.5-187°C) *Chem.Abstr., 49 , 8315b (1955) Example 8 1-Methylthio-1-(p-tolylsulfonyl)
Dissolve 102 mg of cyclobutane in 2.7 ml of ethylene glycol, 0.3 ml of water and 97 mg of sodium bicarbonate.
was added and stirred at 90°C for 7 hours. Hereinafter, cyclobutanone produced in the same manner as in Example 1 was captured with 2,4-dinitrophenylhydrazine, and cyclobutanone 2,4-dinitrophenylhydrazine was separated by silica gel column chromatography.
89.4mg was obtained. Yield 82%. Melting point 146.5-148.0℃ (literature value *146℃) *Chem.Ber., 55 , 2737 (1922)
Claims (1)
ン原子を示す）を、Ｘは酸素原子、硫黄原子また
はメチレン基を、ｍおよびｎは整数を示す〕 で表されるメチルチオメチルアリールスルホン
誘導体を極性溶媒中水の存在下に加熱分解するこ
とを特徴とする 一般式〔２〕 〔式中、Ｘは酸素原子、硫黄原子またはメチレ
ン基を、ｍおよびｎは整数を示す〕 で表される環状ケトン類の製造法。 ２ 加熱分解を塩基存在下に行う特許請求の範囲
第１項の製造法。[Claims] 1 General formula [1] [In the formula, A represents the formula (R represents a hydrogen atom, a lower alkyl group, an alkoxy group, or a halogen atom), X represents an oxygen atom, a sulfur atom, or a methylene group, and m and n represent integers] General formula [2] characterized in that the represented methylthiomethylarylsulfone derivative is thermally decomposed in the presence of water in a polar solvent. [In the formula, X represents an oxygen atom, a sulfur atom, or a methylene group, and m and n represent integers.] A method for producing a cyclic ketone represented by the following. 2. The production method according to claim 1, wherein the thermal decomposition is carried out in the presence of a base.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59011408A JPS60156621A (en) | 1984-01-25 | 1984-01-25 | Preparation of cyclic ketone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59011408A JPS60156621A (en) | 1984-01-25 | 1984-01-25 | Preparation of cyclic ketone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60156621A JPS60156621A (en) | 1985-08-16 |
| JPH058176B2 true JPH058176B2 (en) | 1993-02-01 |
Family
ID=11777187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59011408A Granted JPS60156621A (en) | 1984-01-25 | 1984-01-25 | Preparation of cyclic ketone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60156621A (en) |
-
1984
- 1984-01-25 JP JP59011408A patent/JPS60156621A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60156621A (en) | 1985-08-16 |
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