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Process for Producing 6-Methyl-2-Heptanone Analogues, and Process for Producing Phyton and Isophytol

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Process for Producing 6-Methyl-2-Heptanone Analogues, and Process for Producing Phyton and Isophytol Europäisches Patentamt *EP000816321B1* (19) European Patent Office Office européen des brevets (11) EP 0 816 321 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: C07C 45/74, C07C 45/62, of the grant of the patent: C07C 45/73, C07C 49/04, 05.06.2002 Bulletin 2002/23 C07C 49/203, C07C 33/03 (21) Application number: 97111203.2 (22) Date of filing: 03.07.1997 (54) Process for producing 6-methyl-2-heptanone analogues, and process for producing phyton and isophytol Verfahren zur Herstellung von 6-Methyl-2-Heptanon Analogen, und Verfahren zur Herstellung von Phyton und Isophytol Procédé pour la préparation d’analogues de 6-méthyl-2-heptanone, et procédé pour la préparation de phytone et d’isophytol (84) Designated Contracting States: (56) References cited: AT BE CH DE FR GB IT LI NL EP-A- 0 008 741 EP-A- 0 022 955 EP-A- 0 765 853 DE-C- 823 291 (30) Priority: 05.07.1996 JP 19548096 US-A- 2 485 989 US-A- 2 499 172 11.12.1996 JP 35221496 US-A- 2 809 215 06.03.1997 JP 5135697 • R. HEILMANN ET AL.: "Recherches sur les (43) Date of publication of application: cétones éthyléniques. - V. Isomérie cis-trans 07.01.1998 Bulletin 1998/02 dans les cétones du type R.CH=CH.CO.CH3" BULLETIN DE LA SOCIETE CHIMIQUE DE (60) Divisional application: FRANCE., 1957, PARIS FR, pages 112-118, 01109535.3 / 1 122 236 XP002043076 • M. MOUSSERON-CANET ET AL.: "Vitesses (73) Proprietor: KURARAY CO., LTD. relatives d’ époxydation de quelques molécules Okayama 710 (JP) terpéniques" BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE., 1963, PARIS FR, pages (72) Inventors: 376-378, XP002043077 • Kido, Yoichi • WANNAGAT U ET AL: "Sila perfumes and Kashima-gun, Ibaraki, 314-02 (JP) isosteric perfumes. 13. Isosteric compounds • Kumagai, Noriaki according to the hydride principle of Grimm in Kashima-gun, Ibaraki, 314-02 (JP) the linalool-type of odorous compounds." • Iwasaki, Hideharu MONATSH. CHEM. (MOCMB7,00269247);94; Kashima-gun, Ibaraki, 314-02 (JP) VOL.125 (11); PP.1159-69, TECHNISCHEN UNIV. • Onishi, Takashi BRAUNSCHWEIG;INST. ANORGANISCHE; Kashima-gun, Ibaraki, 314-02 (JP) BRAUNSCHWEIG; D-38106; GERMANY (DE), • Ueyama, Fuyuo XP002043078 Kitakanbara-gun, Niigata, 959-26 (JP) (74) Representative: Müller-Boré & Partner Patentanwälte Grafinger Strasse 2 81671 München (DE) Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 0 816 321 B1 Printed by Jouve, 75001 PARIS (FR) (Cont. next page) EP 0 816 321 B1 • A. OFNER ET AL.: "Synthetisches nerolidol und • AKUTAGAWA S ET AL: "Metal-assisted verwandte C15-alkohole" HELVETICA CHIMICA terpenoid synthesis. V. The catalytic ACTA., vol. XLII, no. VII, 1959, BASEL CH, pages trimerization of isoprene to 2577-2584, XP002043079 trans-.beta.-farnesene and its synthetic applications for terpenoids" BULL. CHEM. SOC. JPN. (BCSJA8,00092673);78; VOL.51 (4); PP.1158-62, TAKASAGO PERFUMERY CO., LTD.;CENT. RES. LAB.; TOKYO; JAPAN, XP002043080 2 EP 0 816 321 B1 Description [0001] This invention relates to a process for producing in an industrially simple manner 6-methyl-2-heptanone an- alogues (e.g., 6-methyl-2-heptanone or 6,10-dimethyl-2-undecanone), which serve as materials for producing phyton 5 or isophytol. This invention also relates to a process for producing phyton or isophytol from the 6-methyl-2-heptanone analogue. [0002] As well known, phyton and isophytol are compounds useful as intermediates for producing biologically active substances such as vitamin E [see Yuki Gosei Kagaku Kyokaishi, 20, 824-836 (1962)] and can be produced by various processes. From the viewpoint of industrial application, a process is considered to be favored in which a ketone having 10 8 carbon atoms represented by the following Formula (I) 15 (the dotted line in the Formula means that one or two carbon-carbon double bond(s) can be present so long as the valence of carbon at the position indicated by such double bond(s) is satisfied) is used as an intermediate (hereinafter the ketone represented by Formula (I) is referred to as "C8 terpene ketone". 20 [0003] Here, in an instance, the whole process for producing phyton and isophytol where 6-methyl-5-hepten-2-one is used as the C8 terpene ketone will be shown by the following scheme. 25 30 35 40 45 50 55 3 EP 0 816 321 B1 5 10 15 20 25 30 35 40 45 50 [0004] Thus, in the process for producing phyton or isophytol from the C8 terpene ketone, it basically proceeds that the principal carbon chain of the C8 terpene ketone is several times made longer by five carbons corresponding to the 55 isoprene unit, followed by hydrogenation of the carbon-carbon double bond in the resulting compound. This basic procedure is not different whether or not unsaturated bonds are present, and at whatever positions they are, in the C8 terpene ketone. Accordingly, in the process for producing phyton or isophytol from C8 terpene ketone, how to produce the intermediate C8 terpene ketone with ease and at a low cost is one of important factors for the industrial application. 4 EP 0 816 321 B1 [0005] In this regard, as processes for producing the C8 terpene ketone, those shown below are known, for example. [0006] Process (i): A process in which acetone ,the starting material, is subjected to ethynylation by acetylene in the presence of an alkaline catalyst to form 3-methyl-1-butyn-3-ol and successive partial hydrogenation in the presence of a Lindlar catalyst, followed by reaction with diketene to form an ester derivative of acetoacetic acid. Thereafter, the 5 ester thus formed is further subjected to Carroll rearrangement to produce 6-methyl-5-hepten-2-one [see, e.g., J. Org. Chem., 23, 153 (1958); Zh. Obshch. Chim., 28, 1444 (1958)]. [0007] Process (ii): A process in which isobutene, acetone and formaldehyde are allowed to react under conditions of a high temperature and a high pressure to give 6-methyl-6-hepten-2-one (see, e.g., German Patents No. 12 59 876 and No. 12 68 135 and U.S. Patent No. 3,574,773). 10 [0008] Process (iii): A process in which prenyl chloride obtained by the reaction of isoprene with hydrogen chloride is allowed to react with acetone in the presence of an equimolar amount of an alkali based on the prenyl chloride to give 6-methyl-5-hepten-2-one (see, e.g., U.S. Patents No. 3,983,175 and No. 3,984,475). [0009] These processes for producing C8 terpene ketone, however, have problems as stated below. [0010] The process (i) has a problem that it requires many steps resulting in a higher production cost. The process 15 (ii) has a problem that it requires special manufacturing equipments because the reaction is carried out under conditions of a high temperature and a high pressure. In the process (iii), the use of an alkali in an equimolar amount based on the prenyl chloride results in the formation of a salt in a large quantity to make it necessary to take much labor for its disposal. [0011] 6-Methyl-2-heptanone is not only useful as a material for producing phyton and isophytol as previously stated, 20 which are intermediates for producing vitamin E, but also useful as a material for producing perfumes such as tetrahy- drolinalool and dihydrogeraniol [see, e.g., Bull. Soc. Chim. Fr., 1586 (1955)]. [0012] As conventional processes for producing 6-methyl-2-heptanone, processes (iv) to (ix) shown below are known. [0013] Process (iv): A process in which an isoamyl halide and an acetoacetic acid ester are subjected to condensation 25 reaction under alkaline conditions, followed by hydrolysis and then decarboxylation (see, e.g., Wagner, "SYNTHETIC ORGANIC CHEMISTRY", p.327, John Wiley & Sons, Inc.). [0014] Process (v): A process in which 6-methyl-5-hepten-2-one or 6-methyl-3,5-heptadien-2-one is subjected to hydrogenation in the presence of a hydrogenation catalyst such as Pd or Ni [see, e.g., European Patent No. 34,804; J. Org. Chem., 42, 1709 (1977); Izv. Akad. Nauk. SSSR. Khim., 10, 2381 (1972)]. 30 [0015] Process (vi): A process in which 6-methyl-2-heptanol is oxidized [see, e.g., Recl. Trav. Chim. Pays-Bas, 28, 116 (1909)]. [0016] Process (vii): A process in which 6-methyl-5-hepten-2-ol is treated with a mixture of 85% phosphoric acid and phosphorus pentoxide [see, Bull. Soc. Chim. Fr., 1799 (1963)]. [0017] Process (viii): A process in which methyl vinyl ketone is subjected to 1,4-addition with an isobutyl magnesium 35 halide [see, Bull. Chem. Soc. Jpn., 38, 29 (1965)]. [0018] Process (ix): A process in which isovaleraldehyde and acetone are allowed to react under a stream of hydro- gen, in the presence of a catalyst comprised of a metal oxide and a metal belonging to Group VIII of the periodic table (See U.S. Patents No. 4,146,581 and No. 4,212,825). [0019] The above processes, however, have problems as discussed below. 40 [0020] In the process (iv), a base is used in an equimolar amount based on the acetoacetic acid ester, so a salt is formed in a large quantity to require much labor for its disposal, resulting in a high cost for the production of the 6-methy- 2-heptanone.
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