KR910018334A - 선형 1,3-디케톤의 제조방법 - Google Patents

선형 1,3-디케톤의 제조방법 Download PDF

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KR910018334A
KR910018334A KR1019910006004A KR910006004A KR910018334A KR 910018334 A KR910018334 A KR 910018334A KR 1019910006004 A KR1019910006004 A KR 1019910006004A KR 910006004 A KR910006004 A KR 910006004A KR 910018334 A KR910018334 A KR 910018334A
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alkyl
phenyl
hydroxy
halogen
hydrogen
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KR1019910006004A
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KR0168056B1 (ko
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드레베스 롤프
헬무트 프리드리히 한스
루드비히 메너 한스
브라운 베른트
베크트 발터
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베르너 발데크
시바-가이기 아게
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    • 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
    • C07C45/72—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 of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • 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
    • C07C45/76—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 with the aid of ketenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

내용 없음

Description

선형 1, 3-디케톤의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (11)

  1. 염기로서 알칼리 금속 또는 알칼리 토금속의 수소화물 또는 알칼기 금속 또는 알칼리 토금속의 C1-C5알코올레이트 존재하에서, 디메틸 술폭시드 및 반응 조건에서 불활성인 하나 이상의 유기 용매의 혼합물 중에서 하기 일반식(Ⅲ)의 케톤을 하기 일반식(Ⅳ)의 에스테르와 클라이센 축합 반응시키거나, 또는 일반식(Ⅰ)중의 R2가 -(CH2)mOH이면 케톤을 하기 일반식(Ⅴ)의 시클릭 에스테르와 클라이센 축합 반응시킴으로써 하기 일반식(Ⅰ)의 선형 1, 3-디케톤을 제조하는 방법.
    상기식에서 R1 및 R2는 서로 독립해서 C1-C20알킬, 페닐 또는 할로겐, 히드록시, NO2, C1-C4알킬 및 또는 C1-C4알콕시에 의해 치환된 페닐이거나, 또는 C7-C9페닐알킬 또는 -A-X-R4(Ⅱ)의 라디칼이고, A는 C1-C12알킬렌, 페닐렌 또는 할로겐, 히드록시, NO2, C1-C4알킬 및/또는 C1-C4알콕시에 의해 치환된 페닐렌이거나, 또는 히드록시, 할로겐 및/또는 알콕시로 치환된 C1-C12알킬렌이며, X는 산소 또는 황이고, R4는 수소, C1-C18알킬, 페닐 또는 할로겐, 히드록시, C1-C4알킬, NO2및/또는 C1-C4알콕시에 의해 치환된 페닐이거나, 또는 C7-C9페닐알킬이며, R3은 수소, C1-C20알킬, 페닐 또는 할로겐, 히드록시, C1-C4알킬, NO2및/또는 C1-C4알콕시에 의해 치환된 페닐이거나, 또는 C7-C9페닐알킬이고, R5는 C1-C5알킬, 페닐 또는 할로겐, C1-C4알킬 또는 히드록시에 의해 치환된 페닐이며, 또 m는 2 내지 10임.
  2. 제1항에 있어서, R1및 R2가 서로 독립해서 C1-C20알킬, 페닐, (C1-C4알킬)페닐 또는 일반식(Ⅱ)의 라디칼이고, A가 C1-C6알킬렌이며, R4가 수소, C1-C18알킬, 페닐 또는 (C1-C4알킬)페닐이고, 또 R3이 수소 및 C1-C4알킬인 일반식(Ⅰ)화합물의 제조방법.
  3. 제2항에 있어서, R1및 R2가 서로 독립해서 C1-C18알킬, 페닐 또는 일반식(Ⅱ)의 라디칼이고, R4가 수소, 페닐 또는 C1-C18알킬이며, 또 R3이 수소인 일반식(Ⅰ)의 화합물의 제조방법.
  4. 제1항에 있어서, 반응 조건에서 불활성인 하나 이상의 유기 용매와의 혼합물 중에서 디메틸 술폭시드의 양이 10 내지 80%인 방법.
  5. 제1항에 있어서, 불활성 용매가 선형 또는 시클릭 에테르, 지방족 또는 방향족 탄화수소 및 시클릭 또는 선형 아미드로 구성된 군으로 부터 선정되는 방법.
  6. 제5항에 있어서, 불활성 용매가 디옥산, 테트라히드로푸란, 디에틸렌글리콜디메틸 에테르, 메틸 삼차 부틸에테르, 톨루엔 및 N-메틸피롤리돈으로 구성된 군으로 부터 선정된 방법.
  7. 제1항에 있어서, 클라이센 축합 반응이 -20 내지 +70℃의 온도 범위에서 실행되는 방법.
  8. 제7항에 있어서, 반응이 -5 내지 +40℃의 온도 범위에서 실행되는 방법.
  9. 제1항에 있어서, 클라이센 축합 반응 시간이 0.5 내지 5시간인 방법.
  10. 제1항에 있어서, 이케톤의 알칼리 금속 염 알칼리 토금속 염을 반응 용액으로부터 직접 석출시키고 단리하며 또 희석 산으로 가수분해시킴으로써 디케톤을 순수하게 하는 수득하는 방법.
  11. 제1항에 있어서, 염기가 나트륨 알코올레이트, 바람직하게는 NaOCH3또는 NaO-t-C4H9, 또는 NaH인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910006004A 1990-04-26 1991-04-12 선형 1,3-디케톤의 제조방법 KR0168056B1 (ko)

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JP (1) JPH04225935A (ko)
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CA (1) CA2041134A1 (ko)
DE (1) DE59106456D1 (ko)
ES (1) ES2077208T3 (ko)
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RU2169143C2 (ru) * 1995-05-25 2001-06-20 Джи. Ди. Сирл Энд Ко. Способ получения 3-галогеналкил-1н-пиразолов
TW200504083A (en) 2003-06-10 2005-02-01 Showa Denko Kk Processes for preparing β-diketone compound, metal complex thereof and metallic compound
JP4744815B2 (ja) * 2003-06-10 2011-08-10 昭和電工株式会社 β−ジケトン化合物、その金属錯体および金属化合物の製造方法
DE102005003057A1 (de) 2005-01-22 2006-07-27 Henkel Kgaa Spritzbare, niedrigviskose Kautschuk-Dämpfungsmassen
GB0719180D0 (en) * 2007-10-02 2007-11-14 Cambrex Karlskoga Ab New process
CN102171200B (zh) * 2008-10-02 2015-09-30 坎布雷卡尔斯库加公司 用于制备二酮类和药物的方法
FR2964964B1 (fr) * 2010-09-20 2013-10-18 Dexera Procede de synthese de composes beta-dicarbonyles

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US3004932A (en) * 1958-01-15 1961-10-17 Dow Chemical Co Unsaturated beta-diketones and polymers and co-polymers thereof
DE1618442A1 (de) * 1967-06-24 1970-12-17 Hoechst Ag Verfahren zur Herstellung von cyclischen ss-Diketonen
DE1618444A1 (de) * 1967-06-24 1971-04-01 Hoechst Ag Verfahren zur Herstellung von ss-Diketonen
US4482745A (en) * 1983-11-02 1984-11-13 American Cyanamid Company Procedure for preparing 1,3-diphenyl-1,3-propanedione

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KR0168056B1 (ko) 1999-03-20
JPH04225935A (ja) 1992-08-14
EP0454623A1 (de) 1991-10-30
ES2077208T3 (es) 1995-11-16
EP0454623B1 (de) 1995-09-13
TW223625B (ko) 1994-05-11
CA2041134A1 (en) 1991-10-27
DE59106456D1 (de) 1995-10-19

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