JPH0421654B2 - - Google Patents
Info
- Publication number
- JPH0421654B2 JPH0421654B2 JP27796385A JP27796385A JPH0421654B2 JP H0421654 B2 JPH0421654 B2 JP H0421654B2 JP 27796385 A JP27796385 A JP 27796385A JP 27796385 A JP27796385 A JP 27796385A JP H0421654 B2 JPH0421654 B2 JP H0421654B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ethyl
- butyl
- propyl
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000006317 isomerization reaction Methods 0.000 claims description 9
- -1 α-methyl-2(E)-propyl hexenoate Chemical compound 0.000 description 48
- 150000001875 compounds Chemical class 0.000 description 34
- 238000000034 method Methods 0.000 description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- DTCZJIDFDTTXSG-VAWYXSNFSA-N Butyl 2-decenoate Chemical compound CCCCCCC\C=C\C(=O)OCCCC DTCZJIDFDTTXSG-VAWYXSNFSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- JACBBOONWJFMBB-MDZDMXLPSA-N butyl (e)-oct-2-enoate Chemical compound CCCCC\C=C\C(=O)OCCCC JACBBOONWJFMBB-MDZDMXLPSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- URRYFCLLPGIYQS-AATRIKPKSA-N (e)-2,3-dimethylpent-2-enoic acid Chemical compound CC\C(C)=C(/C)C(O)=O URRYFCLLPGIYQS-AATRIKPKSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JANHVABKWXGORE-VAWYXSNFSA-N butan-2-yl (e)-dec-2-enoate Chemical compound CCCCCCC\C=C\C(=O)OC(C)CC JANHVABKWXGORE-VAWYXSNFSA-N 0.000 description 1
- OPVSKLFHWQRZKR-BQYQJAHWSA-N butyl (e)-hex-2-enoate Chemical compound CCCCOC(=O)\C=C\CCC OPVSKLFHWQRZKR-BQYQJAHWSA-N 0.000 description 1
- HBFOVXQGANUMIF-ZHACJKMWSA-N butyl (e)-non-2-enoate Chemical compound CCCCCC\C=C\C(=O)OCCCC HBFOVXQGANUMIF-ZHACJKMWSA-N 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- GNJARWZWODMTDR-ZHACJKMWSA-N ethyl (2E)-2-decenoate Chemical compound CCCCCCC\C=C\C(=O)OCC GNJARWZWODMTDR-ZHACJKMWSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- IGXZPBPXLKKJMR-FYWRMAATSA-N heptyl (e)-dec-2-enoate Chemical compound CCCCCCCOC(=O)\C=C\CCCCCCC IGXZPBPXLKKJMR-FYWRMAATSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27796385A JPS62138450A (ja) | 1985-12-12 | 1985-12-12 | α−アルキル−３（Ｅ）−アルケン酸エステル類の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27796385A JPS62138450A (ja) | 1985-12-12 | 1985-12-12 | α−アルキル−３（Ｅ）−アルケン酸エステル類の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62138450A JPS62138450A (ja) | 1987-06-22 |
| JPH0421654B2 true JPH0421654B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-04-13 |
Family
ID=17590712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27796385A Granted JPS62138450A (ja) | 1985-12-12 | 1985-12-12 | α−アルキル−３（Ｅ）−アルケン酸エステル類の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62138450A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4920290B2 (ja) * | 2006-04-18 | 2012-04-18 | 富士フレーバー株式会社 | ２，３−ジヒドロ−２，３，５−トリメチル−６−（１−メチル−２−ブテニル）−４−ｈ−ピラン−４−オンの製造方法およびそれに用いる中間体 |
-
1985
- 1985-12-12 JP JP27796385A patent/JPS62138450A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62138450A (ja) | 1987-06-22 |