JPS6227053B2 - - Google Patents
Info
- Publication number
- JPS6227053B2 JPS6227053B2 JP2940880A JP2940880A JPS6227053B2 JP S6227053 B2 JPS6227053 B2 JP S6227053B2 JP 2940880 A JP2940880 A JP 2940880A JP 2940880 A JP2940880 A JP 2940880A JP S6227053 B2 JPS6227053 B2 JP S6227053B2
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenyl
- cyclohexen
- chloro
- methanol
- zinc
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- -1 6-(4-chlorophenyl)-2-cyclohexen-1-one Chemical compound 0.000 claims description 11
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910001115 Zinc-copper couple Inorganic materials 0.000 claims description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000006298 dechlorination reaction Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- MBOXSXIGVXMZDU-UHFFFAOYSA-N 1-chloro-4-(2-methoxyphenyl)benzene Chemical group COC1=CC=CC=C1C1=CC=C(Cl)C=C1 MBOXSXIGVXMZDU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VPUYJVXAJFILQA-UHFFFAOYSA-N 2-(2-chlorophenyl)cyclohex-2-en-1-one Chemical compound ClC1=C(C=CC=C1)C=1C(CCCC=1)=O VPUYJVXAJFILQA-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DQSIERDAHOVWOS-UHFFFAOYSA-N acetic acid benzene Chemical compound CC(=O)O.C1=CC=CC=C1.C1=CC=CC=C1 DQSIERDAHOVWOS-UHFFFAOYSA-N 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2940880A JPS56125332A (en) | 1980-03-07 | 1980-03-07 | Cyclohexene derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2940880A JPS56125332A (en) | 1980-03-07 | 1980-03-07 | Cyclohexene derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56125332A JPS56125332A (en) | 1981-10-01 |
| JPS6227053B2 true JPS6227053B2 (enrdf_load_stackoverflow) | 1987-06-12 |
Family
ID=12275299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2940880A Granted JPS56125332A (en) | 1980-03-07 | 1980-03-07 | Cyclohexene derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56125332A (enrdf_load_stackoverflow) |
-
1980
- 1980-03-07 JP JP2940880A patent/JPS56125332A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56125332A (en) | 1981-10-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Miller et al. | The addition of trimethylsilyl iodide to some α, β-unsaturated ketones | |
| US4307024A (en) | 1,1,1-Triaryl-2,2,2-trifluoroethanes and process for their synthesis | |
| CA1093097A (en) | Process for the production of cyanopinacolone | |
| EP0418690B1 (de) | Verfahren zur Herstellung von Ironen | |
| JPS6227053B2 (enrdf_load_stackoverflow) | ||
| JPS58110542A (ja) | 塩素化β−ケトエステル | |
| JPS5925779B2 (ja) | 立体異性脂環ジアミンの異性化法 | |
| JPS62201842A (ja) | ３−ヒドロキシシクロペント−４−エン−１−オン類の製造法 | |
| JPH07300445A (ja) | ４−ハロ−２′−ニトロブチロフエノン化合物の製造方法 | |
| JPS629098B2 (enrdf_load_stackoverflow) | ||
| JPS6014033B2 (ja) | ４−メチルオキサゾ−ルの製造法 | |
| Adam et al. | Oxygen functionalization of cyclooctatetraene via singlet oxygenation: synthesis and transformations of anti-7, 8-dioxatricyclo [4.2. 2.02, 5] deca-3, 9-diene, the endoperoxide of the bicyclic valence tautomer of cyclooctatetraene | |
| JP4393839B2 (ja) | １，３−ジ−ハロ置換されたベンゼン誘導体の製造 | |
| JPS6122058A (ja) | ３−（４−フルオロフエノキシ）プロピオニトリル及び該化合物を用いる６−フルオロ−４−クロマノンの製造法 | |
| Lake et al. | Chloromethylation of 1, 2, 4-Trimethylbenzene | |
| US3003001A (en) | Process for the production of 1-vinyl-6-alkoxy-3,4-dihydronaphthalene | |
| Boekelheide et al. | A synthesis of 3-bromoperinaphthanol-7 | |
| Zoretic et al. | Robinson annelation with a β-hydroxyketal in the presence of an acid | |
| Wada et al. | THE WITTIG-TYPE AND THE CLAISEN REARRANGEMENT OF ALLYLIC 3-PHENYLTHLO-2-PROPEN-1-YL ETHERS | |
| JPS60188340A (ja) | ２，３−ジメチルペンタナ−ルの製造方法 | |
| RU2057108C1 (ru) | Способ получения е-5-бромпентена-2 | |
| SU1567565A1 (ru) | Способ получени 1-хлор-4-метилпентан-2-ола | |
| Ryu et al. | Reaction of enol ethers with zinc carbenoid reagents. Cyclopropanation and subsequent isomerization to allylic ethers | |
| JP3634874B2 (ja) | トリフルオロメチルアセチレン誘導体、その製造方法およびその中間体の製造方法 | |
| JPS63258836A (ja) | エテン誘導体の製造方法 |