WO2000001648A3 - Preparation of macrocyclic ketones utilising addition of ketones to alkenes - Google Patents

Preparation of macrocyclic ketones utilising addition of ketones to alkenes Download PDF

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Publication number
WO2000001648A3
WO2000001648A3 PCT/GB1999/001999 GB9901999W WO0001648A3 WO 2000001648 A3 WO2000001648 A3 WO 2000001648A3 GB 9901999 W GB9901999 W GB 9901999W WO 0001648 A3 WO0001648 A3 WO 0001648A3
Authority
WO
WIPO (PCT)
Prior art keywords
ketones
preparation
macrocyclic
alkenes
utilising
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.)
Ceased
Application number
PCT/GB1999/001999
Other languages
French (fr)
Other versions
WO2000001648A2 (en
Inventor
David Munro
Kenneth John Palmer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan Nederland Services BV
Original Assignee
Quest International BV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Quest International BV filed Critical Quest International BV
Priority to EP99928094A priority Critical patent/EP1102736A2/en
Priority to JP2000558054A priority patent/JP2002519396A/en
Publication of WO2000001648A2 publication Critical patent/WO2000001648A2/en
Publication of WO2000001648A3 publication Critical patent/WO2000001648A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
    • 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
    • C07C45/61—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
    • C07C45/62—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 hydrogenation of carbon-to-carbon double or triple bonds
    • 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
    • C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional 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
    • C07C45/61—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
    • C07C45/69—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 addition to carbon-to-carbon double or triple bonds
    • 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
    • C07C45/74—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 combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)

Abstract

The invention provides a process for the preparation of macrocyclic ketones by a reaction sequence wherein one step is the radical addition of ketone to alkene of the form (1), where R3 = H or lower alkyl, R4 = H or lower alkyl, m = 4 to 8, or form (2), where R1 = alkyl, R2 = H or alkyl, n = 4 to 8. The process can be used to produce macrocyclic ketone mixtures, particularly those containing muscone which are useful in producing fragranced products.
PCT/GB1999/001999 1998-07-06 1999-06-25 Preparation of macrocyclic ketones utilising addition of ketones to alkenes Ceased WO2000001648A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP99928094A EP1102736A2 (en) 1998-07-06 1999-06-25 Preparation of macrocyclic ketones utilising addition of ketones to alkenes
JP2000558054A JP2002519396A (en) 1998-07-06 1999-06-25 Preparation of macrocyclic ketones utilizing addition of ketones to alkenes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP98305368A EP0976714A1 (en) 1998-07-06 1998-07-06 Addition of ketones to alkenes
EP98305368.7 1998-07-06

Publications (2)

Publication Number Publication Date
WO2000001648A2 WO2000001648A2 (en) 2000-01-13
WO2000001648A3 true WO2000001648A3 (en) 2000-04-13

Family

ID=8234917

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1999/001999 Ceased WO2000001648A2 (en) 1998-07-06 1999-06-25 Preparation of macrocyclic ketones utilising addition of ketones to alkenes

Country Status (3)

Country Link
EP (2) EP0976714A1 (en)
JP (1) JP2002519396A (en)
WO (1) WO2000001648A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10023886A1 (en) 2000-05-17 2001-11-22 Basf Ag Acetoacetic acid derivatives, process for their preparation and their use
EP1608626A1 (en) 2003-03-28 2005-12-28 Cornell Research Foundation, Inc. Migrastatin analog compositions and uses thereof
JP5149001B2 (en) 2004-05-25 2013-02-20 スローン−ケッタリング・インスティテュート・フォー・キャンサー・リサーチ Migrastatin analogues in the treatment of cancer
US8188141B2 (en) 2004-09-23 2012-05-29 Sloan-Kettering Institute For Cancer Research Isomigrastatin analogs in the treatment of cancer
US8940940B2 (en) * 2012-06-13 2015-01-27 Basf Se Process for preparing macrocyclic ketones
CN118221504A (en) * 2024-03-22 2024-06-21 宏济堂制药(商河)有限公司 A preparation method of 14-methyl-2-hydroxy-cyclopentadecanone impurity and reference substance thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1757830A (en) * 1926-07-31 1930-05-06 Commercial Solvents Corp Production of ketones
EP0400509A1 (en) * 1989-06-02 1990-12-05 BASF Aktiengesellschaft Process for the production of muscone, intermediates for this process and their preparation
WO1998009933A1 (en) * 1996-09-02 1998-03-12 Quest International B.V. Substituted 2-cyclohexyl-propan-1-ol and its use in perfume compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1757830A (en) * 1926-07-31 1930-05-06 Commercial Solvents Corp Production of ketones
EP0400509A1 (en) * 1989-06-02 1990-12-05 BASF Aktiengesellschaft Process for the production of muscone, intermediates for this process and their preparation
WO1998009933A1 (en) * 1996-09-02 1998-03-12 Quest International B.V. Substituted 2-cyclohexyl-propan-1-ol and its use in perfume compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CITTERIO, A. ET AL.: "Addition of Ketones to Olefins by Ag+-catalysed Decomposition of Peroxydisulphate", JOURNAL OF CHEMICAL RESEARCH (MINIPRINT), no. 12, December 1983 (1983-12-01), pages 2669 - 2683, XP002087776 *

Also Published As

Publication number Publication date
EP1102736A2 (en) 2001-05-30
WO2000001648A2 (en) 2000-01-13
JP2002519396A (en) 2002-07-02
EP0976714A1 (en) 2000-02-02

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