GB981702A - The manufacture of ª†,ª€-unsaturated aldehydes and ketones - Google Patents

The manufacture of ª†,ª€-unsaturated aldehydes and ketones

Info

Publication number
GB981702A
GB981702A GB26737/63A GB2673763A GB981702A GB 981702 A GB981702 A GB 981702A GB 26737/63 A GB26737/63 A GB 26737/63A GB 2673763 A GB2673763 A GB 2673763A GB 981702 A GB981702 A GB 981702A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
saturated
formula
group
unsaturated aliphatic
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
Application number
GB26737/63A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB981702A publication Critical patent/GB981702A/en
Expired 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
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen 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
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C47/263—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups acyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises g ,d -unsaturated aldehydes having at least 8 carbon atoms of the formula <FORM:0981702/C2/1> in which R1 is a saturated or unsaturated aliphatic group (which may carry a free, esterified or etherified hydroxyl group), an aralkyl group or an aryl group, R2 is a saturated or unsaturated aliphatic group containing 1-8 carbon atoms, or R1 and R2 together may form a carbocyclic group with the carbon atom to which they are attached; R3 is a hydrogen atom or a saturated or unsaturated aliphatic group containing 1-8 carbon atoms and R4 is hydrogen or a saturated or unsaturated aliphatic group containing 1-8 carbon atoms; and 2-[31 - methyl - 21 - butenyl - (1)] - cyclohexanone. The aldehydes and ketones of formula <FORM:0981702/C2/2> in which R5 is hydrogen or a saturated or unsaturated aliphatic group containing 1-8 carbon atoms or forms a carbocyclic group with C4, may be prepared by heating a tertiary allyl alcohol of formula <FORM:0981702/C2/3> with either an enol ether of the formula CH(R4) = C(R5)-OR6 or an acetal or ketal of the formula <FORM:0981702/C2/4> in which R6 is an alkyl group, in the presence of an acidic catalyst. The esterified hydroxy groups referred to include acyloxy groups in which the acyl group is derived from an aliphatic or aromatic carboxylic and the preferred etherified groups are alkoxy groups containing 1-8 carbon atoms and aryloxy groups. The preferred acidic catalyst is phosphoric acid but other suitable catalysts are sulphuric acid, oxalic acid, trichloracetic acid, paratoluene sulphonic acid, potassium bisulphite, boron-trichloride, boron trifluoride and zinc chloride. The preferred temperature range for the process is 120-200 DEG C. The process may be carried out in the presence of a solvent, e.g. hexane, cyclohexane, iso-octane, benzene, toluene, petroleum ether, and ligroin.
GB26737/63A 1962-07-11 1963-07-05 The manufacture of ª†,ª€-unsaturated aldehydes and ketones Expired GB981702A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH833962A CH416596A (en) 1962-07-11 1962-07-11 Process for the preparation of unsaturated carbonyl compounds

Publications (1)

Publication Number Publication Date
GB981702A true GB981702A (en) 1965-01-27

Family

ID=4338801

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26737/63A Expired GB981702A (en) 1962-07-11 1963-07-05 The manufacture of ª†,ª€-unsaturated aldehydes and ketones

Country Status (8)

Country Link
BE (1) BE634738A (en)
BR (1) BR6350354D0 (en)
CH (1) CH416596A (en)
DE (1) DE1193490B (en)
DK (2) DK129697B (en)
ES (1) ES289885A1 (en)
GB (1) GB981702A (en)
NL (1) NL295084A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6184420B1 (en) 1997-09-10 2001-02-06 Basf Aktiengesellschaft Preparation of unsaturated ketones
JP2010535730A (en) * 2007-08-08 2010-11-25 ディーエスエム アイピー アセッツ ビー．ブイ． Method for preparing (E, E) -farnesyl acetone
JP2014532065A (en) * 2011-10-11 2014-12-04 ヴェ マン フィユＶ． Ｍａｎｅ Ｆｉｌｓ Novel cycloalkanealdehyde, its preparation method and its use in the perfume industry
GB2515128A (en) * 2013-06-10 2014-12-17 Givaudan Sa Improvements in or relating to organic compounds
WO2015117893A1 (en) * 2014-02-07 2015-08-13 Dsm Ip Assets B.V. Flavor and fragrance formulation (vii)
WO2016091895A1 (en) * 2014-12-09 2016-06-16 Givaudan Sa Improvements in or relating to organic compounds and their use as flagrance ingredients
WO2016091894A1 (en) * 2014-12-09 2016-06-16 Givaudan Sa Improvements in or relating to organic compounds
WO2016091899A1 (en) * 2014-12-09 2016-06-16 Givaudan Sa Enamine and/or aminal fragance precursors derived from (e/z)-9-hydroxy-5,9-dimethyldec-4-enal
US9850191B2 (en) 2015-03-27 2017-12-26 International Flavors & Fragrances Inc. Aldehyde compounds and their use in perfume compositions
CN113004146A (en) * 2021-03-23 2021-06-22 昆明博鸿生物科技有限公司 Method for preparing olefine aldehyde by catalyzing and oxidizing enol ether

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4057515A (en) * 1969-02-04 1977-11-08 N.V. Chemische Fabriek "Naarden" Perfume compositions
CH527897A (en) * 1969-04-26 1972-09-15 Givaudan & Cie Sa Novel aldehydes unsaturated in gamma or - delta posn
CH566277A5 (en) * 1972-01-21 1975-09-15 Givaudan & Cie Sa
US4292454A (en) 1977-12-29 1981-09-29 Scm Corporation Coupling reaction involving a Grignard and allylic halide
JPS5772931A (en) * 1980-10-24 1982-05-07 Takasago Corp 5-methyl-gamma,delta-unsaturated aldehyde compound
DE3722807A1 (en) * 1987-07-10 1989-01-19 Hoechst Ag NEW 3,5-DIHYDROXYCARBONIC ACIDS AND THEIR DERIVATIVES, PROCESS FOR THEIR PRODUCTION, THEIR USE AS MEDICINAL PRODUCTS, PHARMACEUTICAL PREPARATIONS AND INTERMEDIATE PRODUCTS
DE19649564A1 (en) * 1996-11-29 1998-06-04 Basf Ag Process for the production of gamma, delta-unsaturated ketones by reacting tertiary allyl alcohols with alkenyl alkyl ethers
JP4733057B2 (en) * 2004-02-04 2011-07-27 ディーエスエム アイピー アセッツ ビー．ブイ． Method for producing methylheptenone
WO2012025559A2 (en) 2010-08-24 2012-03-01 Dsm Ip Assets B.V. Process for the manufacture of 3,7-dimethyl-1-octen-3-ol
MY175343A (en) 2012-12-18 2020-06-22 Dsm Ip Assets Bv Efficient process of asymmetric hydrogenation of unsaturated ketones using additives
MY195029A (en) 2012-12-18 2023-01-04 Dsm Ip Assets Bv (6R,10R)-6,10,14-Trimetylpentadecan-2-One Prepared From 6,10-Dimetylundeca-3,5,9-Trien-2-One
WO2014096107A1 (en) 2012-12-18 2014-06-26 Dsm Ip Assets B.V. Using mixtures of e/z isomers to obtain quantitatively specific products by combining asymmetric hydrogenation and isomerization

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH342947A (en) * 1955-04-19 1959-12-15 Hoffmann La Roche Process for the production of unsaturated ketones
US2947786A (en) * 1958-04-14 1960-08-02 Eastman Kodak Co Substituted unsaturated aldehydes
GB865478A (en) * 1958-08-01 1961-04-19 Hoffmann La Roche A process for the manufacture of unsaturated ketones

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6184420B1 (en) 1997-09-10 2001-02-06 Basf Aktiengesellschaft Preparation of unsaturated ketones
JP2010535730A (en) * 2007-08-08 2010-11-25 ディーエスエム アイピー アセッツ ビー．ブイ． Method for preparing (E, E) -farnesyl acetone
JP2014532065A (en) * 2011-10-11 2014-12-04 ヴェ マン フィユＶ． Ｍａｎｅ Ｆｉｌｓ Novel cycloalkanealdehyde, its preparation method and its use in the perfume industry
US10315976B2 (en) 2013-01-10 2019-06-11 Givaudan S.A. Organic compounds
RU2667901C2 (en) * 2013-06-10 2018-09-25 Живодан Са Improvements in or relating to organic compounds
CN112661622A (en) * 2013-06-10 2021-04-16 奇华顿股份有限公司 Improvements in or relating to organic compounds
GB2515128A (en) * 2013-06-10 2014-12-17 Givaudan Sa Improvements in or relating to organic compounds
CN105283435A (en) * 2013-06-10 2016-01-27 奇华顿股份有限公司 Improvements in or relating to organic compounds
KR20160019441A (en) * 2013-06-10 2016-02-19 지보당 에스아 Improvements in or relating to organic compounds
CN105283435B (en) * 2013-06-10 2021-12-21 奇华顿股份有限公司 Improvements in or relating to organic compounds
GB2515128B (en) * 2013-06-10 2015-05-27 Givaudan Sa Improvements in or relating to organic compounds
WO2014198709A1 (en) 2013-06-10 2014-12-18 Givaudan Sa Improvements in or relating to organic compounds
JP2016521739A (en) * 2013-06-10 2016-07-25 ジボダン エス エー Improvements in or relating to organic compounds
AU2014280241B2 (en) * 2013-06-10 2017-12-21 Givaudan Sa Improvements in or relating to organic compounds
US9469590B2 (en) 2013-06-10 2016-10-18 Givaudan S.A. Organic compounds
US20160340285A1 (en) * 2014-02-07 2016-11-24 Dsm Ip Assets B.V. Flavor and fragrance formulation (vii)
CN105979792A (en) * 2014-02-07 2016-09-28 帝斯曼知识产权资产管理有限公司 Flavor and fragrance formulation (vii)
WO2015117893A1 (en) * 2014-02-07 2015-08-13 Dsm Ip Assets B.V. Flavor and fragrance formulation (vii)
WO2016091894A1 (en) * 2014-12-09 2016-06-16 Givaudan Sa Improvements in or relating to organic compounds
US10351797B2 (en) 2014-12-09 2019-07-16 Givaudan Sa Enamine and/or aminal fragrance precursors derived from (E/Z)-9-hydroxy-5,9-di-methyldec-4-enal
US10450532B2 (en) 2014-12-09 2019-10-22 Givaudan S.A. Organic compounds and their use as fragrance ingredients
WO2016091899A1 (en) * 2014-12-09 2016-06-16 Givaudan Sa Enamine and/or aminal fragance precursors derived from (e/z)-9-hydroxy-5,9-dimethyldec-4-enal
WO2016091895A1 (en) * 2014-12-09 2016-06-16 Givaudan Sa Improvements in or relating to organic compounds and their use as flagrance ingredients
US9850191B2 (en) 2015-03-27 2017-12-26 International Flavors & Fragrances Inc. Aldehyde compounds and their use in perfume compositions
CN113004146A (en) * 2021-03-23 2021-06-22 昆明博鸿生物科技有限公司 Method for preparing olefine aldehyde by catalyzing and oxidizing enol ether

Also Published As

Publication number Publication date
DE1193490B (en) 1965-05-26
BE634738A (en) 1900-01-01
CH416596A (en) 1966-07-15
DK129697C (en) 1975-04-21
ES289885A1 (en) 1963-10-16
DK129697B (en) 1974-11-11
NL295084A (en) 1900-01-01
BR6350354D0 (en) 1973-08-16
DK126643B (en) 1973-08-06

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