JPS6121941B2 - - Google Patents
Info
- Publication number
- JPS6121941B2 JPS6121941B2 JP20684684A JP20684684A JPS6121941B2 JP S6121941 B2 JPS6121941 B2 JP S6121941B2 JP 20684684 A JP20684684 A JP 20684684A JP 20684684 A JP20684684 A JP 20684684A JP S6121941 B2 JPS6121941 B2 JP S6121941B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- butane
- dimethylamino
- acid
- triethoxy
- 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
Links
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 20
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 7
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 7
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 claims description 7
- 229930007744 linalool Natural products 0.000 claims description 7
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical class CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- -1 geranyl acetic acids Chemical class 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 235000011054 acetic acid Nutrition 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- WLAUCMCTKPXDIY-JXMROGBWSA-N (2e)-1-chloro-3,7-dimethylocta-2,6-diene Chemical compound CC(C)=CCC\C(C)=C\CCl WLAUCMCTKPXDIY-JXMROGBWSA-N 0.000 description 3
- WIHSFNRKGXNWNK-NTCAYCPXSA-N (4e)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid Chemical compound CC(C)=CCC\C(C)=C\CC(C(O)=O)C1CCCCC1 WIHSFNRKGXNWNK-NTCAYCPXSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- HPOYZGTYWKRTPU-DHZHZOJOSA-N (4e)-5,9-dimethyldeca-4,8-dienoic acid Chemical compound CC(C)=CCC\C(C)=C\CCC(O)=O HPOYZGTYWKRTPU-DHZHZOJOSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 208000004210 Pressure Ulcer Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminum chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- NUYCINUWJWAOFR-UHFFFAOYSA-N ethyl 2-cyano-2-cyclohexylacetate Chemical compound CCOC(=O)C(C#N)C1CCCCC1 NUYCINUWJWAOFR-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- IDFANOPDMXWIOP-UHFFFAOYSA-N n,n-dimethylpentan-1-amine Chemical compound CCCCCN(C)C IDFANOPDMXWIOP-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- WQSRXNAKUYIVET-UHFFFAOYSA-N sulfuric acid;zinc Chemical compound [Zn].OS(O)(=O)=O WQSRXNAKUYIVET-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20684684A JPS615060A (ja) | 1984-10-01 | 1984-10-01 | 2−置換のゲラニル酢酸エステルの製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20684684A JPS615060A (ja) | 1984-10-01 | 1984-10-01 | 2−置換のゲラニル酢酸エステルの製造方法 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP49134801A Division JPS5855129B2 (ja) | 1974-11-21 | 1974-11-21 | 2−置換または無置換のゲラニル酢酸エステル類の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS615060A JPS615060A (ja) | 1986-01-10 |
JPS6121941B2 true JPS6121941B2 (de) | 1986-05-29 |
Family
ID=16530023
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP20684684A Granted JPS615060A (ja) | 1984-10-01 | 1984-10-01 | 2−置換のゲラニル酢酸エステルの製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS615060A (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02120677U (de) * | 1989-03-14 | 1990-09-28 | ||
JPH0514839B2 (de) * | 1987-09-14 | 1993-02-26 | Tlv Co Ltd |
-
1984
- 1984-10-01 JP JP20684684A patent/JPS615060A/ja active Granted
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0514839B2 (de) * | 1987-09-14 | 1993-02-26 | Tlv Co Ltd | |
JPH02120677U (de) * | 1989-03-14 | 1990-09-28 |
Also Published As
Publication number | Publication date |
---|---|
JPS615060A (ja) | 1986-01-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Cope et al. | The introduction of substituted vinyl Groups. V. A rearrangement involving the Migration of an Allyl Group in a Three-Carbon System1 | |
US4740613A (en) | Preparation of 4-pentenoates | |
JP2004203844A (ja) | 2−(アルキリデン)シクロアルカノンの製法 | |
CN100364950C (zh) | 2-(烷基)环烯酮的制备方法 | |
JPS6193135A (ja) | 新規光学活性アリ−ルアルカノン化合物およびこれを用いるナプロクセンの製造方法 | |
JPS6121941B2 (de) | ||
US4970345A (en) | Process for preparing oxocyclopentene derivatives | |
JP4407896B2 (ja) | 2−(アルキル)シクロアルケノンの製法 | |
Hyuga et al. | Organic Synthesis Using Haloboration Reaction. XXI. A Synthesis of Prostaglandin B1 Methyl Ester by the Stepwise Cross-Coupling Reaction Using (E)-(2-Bromoethenyl) diisopropoxyborane. | |
JPH11292812A (ja) | トリメチルヒドロキノンジエステル及び2,3,5―トリメチルヒドロキノンの製法 | |
JPS5855129B2 (ja) | 2−置換または無置換のゲラニル酢酸エステル類の製造方法 | |
Slegeris et al. | Alternative synthetic approaches to rac-progesterone by way of the classic Johnson cationic polycyclization strategy | |
JPH0559116B2 (de) | ||
Seo et al. | An improved practical synthesis of isomerically pure 3-endo-(p-Methoxybenzyl) isoborneol | |
EP0194849B1 (de) | Verfahren zur Herstellung von aromatischen N-Acyl-acyloxy-aminen | |
JPS6140227A (ja) | イソブチルベンゼンの製造方法 | |
JP4418048B2 (ja) | 13−シス−レチノイン酸の製造方法 | |
US2987551A (en) | Preparation of citral | |
US2369162A (en) | Synthesis of vitamin a | |
JP2974327B2 (ja) | ポリアルキル―2―アルコキシ―7―ヒドロキシクロマンの製造方法 | |
JPH0959208A (ja) | ローズフラン前駆体の製造方法及びその中間体 | |
JP2541197B2 (ja) | 光学活性シクロペンテン誘導体とその製法 | |
Ames et al. | Syntheses of long-chain acids. Part VIII. 9, 10, 18-Trihydroxyoctadecanoic acids | |
JP5817574B2 (ja) | cis−3−ヘキセナールの蒸留方法 | |
HU200582B (en) | New process for producing dihydroxyacyl benzenes as intermediate products of leukotriene antagonists |