JPH0246590B2 - - Google Patents
Info
- Publication number
- JPH0246590B2 JPH0246590B2 JP55125401A JP12540180A JPH0246590B2 JP H0246590 B2 JPH0246590 B2 JP H0246590B2 JP 55125401 A JP55125401 A JP 55125401A JP 12540180 A JP12540180 A JP 12540180A JP H0246590 B2 JPH0246590 B2 JP H0246590B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- muscone
- methylbicyclo
- oxa
- 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
- -1 cyclic diol Chemical class 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 claims description 5
- 229910000831 Steel Inorganic materials 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- 239000010959 steel Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 16
- ALHUZKCOMYUFRB-UHFFFAOYSA-N muskone Natural products CC1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-UHFFFAOYSA-N 0.000 description 16
- ALHUZKCOMYUFRB-OAHLLOKOSA-N Muscone Chemical compound C[C@@H]1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-OAHLLOKOSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000002084 enol ethers Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH829379A CH642373A5 (fr) | 1979-09-13 | 1979-09-13 | Compose pyrannique, procede pour sa preparation et son utilisation a titre d'intermediaire de synthese. |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2125622A Division JPH03115246A (ja) | 1979-09-13 | 1990-05-17 | ムスコンの製法及び不飽和大環状ケトンの製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5646881A JPS5646881A (en) | 1981-04-28 |
| JPH0246590B2 true JPH0246590B2 (US07122547-20061017-C00224.png) | 1990-10-16 |
Family
ID=4338073
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12540180A Granted JPS5646881A (en) | 1979-09-13 | 1980-09-11 | Manufacture of muscone* novel pyran derivative* its manufacture and manufacture of unsaturated macrocyclic ketone |
| JP2125622A Pending JPH03115246A (ja) | 1979-09-13 | 1990-05-17 | ムスコンの製法及び不飽和大環状ケトンの製法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2125622A Pending JPH03115246A (ja) | 1979-09-13 | 1990-05-17 | ムスコンの製法及び不飽和大環状ケトンの製法 |
Country Status (7)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4605500A (en) * | 1984-04-24 | 1986-08-12 | Mitsubishi Rayon Co., Ltd. | Hollow-fiber filter module |
| EP0584477B1 (fr) * | 1992-07-30 | 1997-09-24 | Firmenich Sa | Utilisation d'une cyclopentadécénone à titre d'ingrédient parfumant |
| US10196332B2 (en) | 2015-09-22 | 2019-02-05 | Basf Se | Process for preparing 3-methylcyclopentadecane-1,5-diol |
| EP3170828A1 (de) * | 2015-11-23 | 2017-05-24 | Basf Se | Verfahren zur herstellung von verbindungen mit 16-oxabicyclo[10.3.1]pentadecengerüst und deren folgeprodukten |
| JP7039551B2 (ja) * | 2016-07-15 | 2022-03-22 | ビーエーエスエフ ソシエタス・ヨーロピア | ３－メチル－１，５－シクロペンタデカンジオンからの１４－メチル－１６－オキサビシクロ［１０．３．１］ペンタデセンの調製 |
| WO2020066898A1 (ja) * | 2018-09-28 | 2020-04-02 | 花王株式会社 | 環状エノールエーテル化合物の製造方法 |
| US11753417B2 (en) | 2019-01-17 | 2023-09-12 | International Flavors & Fragrances Inc. | Synthesis of 14-methyl-16-oxabicyclo[10.3.1]hexadec-12-ene |
| CN113614058B (zh) | 2019-03-18 | 2024-09-27 | 花王株式会社 | 制备α-烯丙基化环烷酮的方法 |
| CN113614057B (zh) * | 2019-03-18 | 2024-09-27 | 花王株式会社 | 制备α-烯丙基化环烷酮的方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6041655A (ja) * | 1983-07-19 | 1985-03-05 | アメリカン・サイアナミド・カンパニ− | 尿素類およびチオ尿素類、それらの製造法並びに医薬用途 |
| JPS6043353A (ja) * | 1983-07-27 | 1985-03-07 | ゼネラル・フ−ヅ・コ−ポレ−シヨン | 再水和性米製品 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929893A (en) * | 1970-12-29 | 1975-12-30 | Takasago Perfumery Co Ltd | Process for preparing cyclohexadecenone-5 |
| GB1492525A (en) * | 1973-11-14 | 1977-11-23 | Shell Int Research | Cyclic alkanones |
| US4277625A (en) * | 1978-12-07 | 1981-07-07 | Firmenich Sa | Process for the preparation of muscone |
-
1979
- 1979-09-13 CH CH374483A patent/CH642342A5/fr not_active IP Right Cessation
- 1979-09-13 CH CH829379A patent/CH642373A5/fr not_active IP Right Cessation
-
1980
- 1980-09-03 US US06/183,722 patent/US4335262A/en not_active Expired - Lifetime
- 1980-09-10 DE DE3050772A patent/DE3050772C2/de not_active Expired
- 1980-09-10 DE DE3034040A patent/DE3034040C2/de not_active Expired
- 1980-09-10 NL NL8005094A patent/NL8005094A/nl not_active Application Discontinuation
- 1980-09-11 JP JP12540180A patent/JPS5646881A/ja active Granted
- 1980-09-12 FR FR8019801A patent/FR2464936A1/fr active Granted
- 1980-09-12 GB GB8629492A patent/GB2058786B/en not_active Expired
-
1981
- 1981-02-11 FR FR8102699A patent/FR2475045A1/fr active Granted
- 1981-11-20 US US06/323,578 patent/US4480107A/en not_active Expired - Fee Related
-
1983
- 1983-06-10 GB GB08315918A patent/GB2125397B/en not_active Expired
-
1990
- 1990-05-17 JP JP2125622A patent/JPH03115246A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6041655A (ja) * | 1983-07-19 | 1985-03-05 | アメリカン・サイアナミド・カンパニ− | 尿素類およびチオ尿素類、それらの製造法並びに医薬用途 |
| JPS6043353A (ja) * | 1983-07-27 | 1985-03-07 | ゼネラル・フ−ヅ・コ−ポレ−シヨン | 再水和性米製品 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2475045B1 (US07122547-20061017-C00224.png) | 1983-05-20 |
| JPH03115246A (ja) | 1991-05-16 |
| US4480107A (en) | 1984-10-30 |
| GB8315918D0 (en) | 1983-07-13 |
| DE3050772C2 (US07122547-20061017-C00224.png) | 1989-03-09 |
| DE3034040C2 (de) | 1987-04-30 |
| NL8005094A (nl) | 1981-03-17 |
| GB2125397B (en) | 1984-08-01 |
| FR2475045A1 (fr) | 1981-08-07 |
| GB2058786B (en) | 1984-03-14 |
| JPS5646881A (en) | 1981-04-28 |
| US4335262A (en) | 1982-06-15 |
| CH642342A5 (fr) | 1984-04-13 |
| FR2464936B1 (US07122547-20061017-C00224.png) | 1983-02-11 |
| DE3034040A1 (de) | 1981-04-02 |
| GB2058786A (en) | 1981-04-15 |
| CH642373A5 (fr) | 1984-04-13 |
| GB2125397A (en) | 1984-03-07 |
| FR2464936A1 (fr) | 1981-03-20 |
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