JPS6335614B2 - - Google Patents
Info
- Publication number
- JPS6335614B2 JPS6335614B2 JP61026552A JP2655286A JPS6335614B2 JP S6335614 B2 JPS6335614 B2 JP S6335614B2 JP 61026552 A JP61026552 A JP 61026552A JP 2655286 A JP2655286 A JP 2655286A JP S6335614 B2 JPS6335614 B2 JP S6335614B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- cyclohexadienone
- methyl
- cyclohexadiene
- methylidene
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical class C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- -1 aliphatic ethers Chemical class 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- 239000012043 crude product Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- KTIXOQCHPJCHEA-UHFFFAOYSA-N 1,3,5,6,6-pentamethoxy-3-methylcyclohexa-1,4-diene Chemical compound COC1=CC(C)(OC)C=C(OC)C1(OC)OC KTIXOQCHPJCHEA-UHFFFAOYSA-N 0.000 description 2
- MSKKDGNGCDTSJT-UHFFFAOYSA-N 1,5,6,6-tetramethoxy-3-methylidenecyclohexa-1,4-diene Chemical compound COC1=CC(=C)C=C(OC)C1(OC)OC MSKKDGNGCDTSJT-UHFFFAOYSA-N 0.000 description 2
- OQLNIPQHMKAAFO-UHFFFAOYSA-N 2,4,6-trimethoxy-4-methylcyclohexa-2,5-dien-1-one Chemical compound COC1=CC(C)(OC)C=C(OC)C1=O OQLNIPQHMKAAFO-UHFFFAOYSA-N 0.000 description 2
- GZJCVPKMBKGCPD-UHFFFAOYSA-N 2,6-diethoxy-4-methylidenecyclohexa-2,5-dien-1-one Chemical compound CCOC1=CC(=C)C=C(OCC)C1=O GZJCVPKMBKGCPD-UHFFFAOYSA-N 0.000 description 2
- DOHBOMUAJSYBTA-UHFFFAOYSA-N 2,6-dimethoxy-4-methylidenecyclohexa-2,5-dien-1-one Chemical compound COC1=CC(=C)C=C(OC)C1=O DOHBOMUAJSYBTA-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- UPYZVCJEJPOBLP-UHFFFAOYSA-N 1,3,5,6,6-pentaethoxy-3-methylcyclohexa-1,4-diene Chemical compound CCOC1=CC(C)(OCC)C=C(OCC)C1(OCC)OCC UPYZVCJEJPOBLP-UHFFFAOYSA-N 0.000 description 1
- VUMWHYCXDQZOMR-UHFFFAOYSA-N 1,5,6-tributoxy-6-methoxy-3-methylidenecyclohexa-1,4-diene Chemical compound CCCCOC1=CC(=C)C=C(OCCCC)C1(OC)OCCCC VUMWHYCXDQZOMR-UHFFFAOYSA-N 0.000 description 1
- WBUZNJFUZOQENT-UHFFFAOYSA-N 1,5,6-triethoxy-6-methoxy-3-methylidenecyclohexa-1,4-diene Chemical compound CCOC1=CC(=C)C=C(OCC)C1(OC)OCC WBUZNJFUZOQENT-UHFFFAOYSA-N 0.000 description 1
- WDFNDYFLIMIPIK-UHFFFAOYSA-N 1-ethoxy-3-methylidenecyclohexa-1,4-diene Chemical compound C(C)OC1=CC(C=CC1)=C WDFNDYFLIMIPIK-UHFFFAOYSA-N 0.000 description 1
- JABFMZKEZLNFNY-UHFFFAOYSA-N 2,4,6-triethoxy-4-methylcyclohexa-2,5-dien-1-one Chemical compound CCOC1=CC(C)(OCC)C=C(OCC)C1=O JABFMZKEZLNFNY-UHFFFAOYSA-N 0.000 description 1
- VCNVSUFOKYRQQZ-UHFFFAOYSA-N 2,6-dibutoxy-4-ethoxy-4-methylcyclohexa-2,5-dien-1-one Chemical compound CCCCOC1=CC(C)(OCC)C=C(OCCCC)C1=O VCNVSUFOKYRQQZ-UHFFFAOYSA-N 0.000 description 1
- IMTWOBKKFHWPNA-UHFFFAOYSA-N 2,6-dibutoxy-4-methoxy-4-methylcyclohexa-2,5-dien-1-one Chemical compound CCCCOC1=CC(C)(OC)C=C(OCCCC)C1=O IMTWOBKKFHWPNA-UHFFFAOYSA-N 0.000 description 1
- WDUWSFJISJMFJV-UHFFFAOYSA-N 2,6-diethoxy-4-methoxy-4-methylcyclohexa-2,5-dien-1-one Chemical compound CCOC1=CC(C)(OC)C=C(OCC)C1=O WDUWSFJISJMFJV-UHFFFAOYSA-N 0.000 description 1
- NVMXMHDEFRSANN-UHFFFAOYSA-N 2,6-diethoxy-4-methyl-4-propoxycyclohexa-2,5-dien-1-one Chemical compound CCCOC1(C)C=C(OCC)C(=O)C(OCC)=C1 NVMXMHDEFRSANN-UHFFFAOYSA-N 0.000 description 1
- XSSYMGSEFTVTBG-UHFFFAOYSA-N 3,6-diethoxy-1,5,6-trimethoxy-3-methylcyclohexa-1,4-diene Chemical compound CCOC1(C)C=C(OC)C(OC)(OCC)C(OC)=C1 XSSYMGSEFTVTBG-UHFFFAOYSA-N 0.000 description 1
- XCDGHOSZCIWEGN-UHFFFAOYSA-N 4-butoxy-2,6-diethoxy-4-methylcyclohexa-2,5-dien-1-one Chemical compound CCCCOC1(C)C=C(OCC)C(=O)C(OCC)=C1 XCDGHOSZCIWEGN-UHFFFAOYSA-N 0.000 description 1
- JOKUBPDQACIRLU-UHFFFAOYSA-N 4-butoxy-2,6-dimethoxy-4-methylcyclohexa-2,5-dien-1-one Chemical compound CCCCOC1(C)C=C(OC)C(=O)C(OC)=C1 JOKUBPDQACIRLU-UHFFFAOYSA-N 0.000 description 1
- UNAVUMKHKMTXBT-UHFFFAOYSA-N 4-ethoxy-2,6-dimethoxy-4-methylcyclohexa-2,5-dien-1-one Chemical compound CCOC1(C)C=C(OC)C(=O)C(OC)=C1 UNAVUMKHKMTXBT-UHFFFAOYSA-N 0.000 description 1
- WKSYNYCTULFLGK-UHFFFAOYSA-N 4-ethoxy-4-methyl-2,6-dipropoxycyclohexa-2,5-dien-1-one Chemical compound CCCOC1=CC(C)(OCC)C=C(OCCC)C1=O WKSYNYCTULFLGK-UHFFFAOYSA-N 0.000 description 1
- VUFGBBBKZZPLKV-UHFFFAOYSA-N 4-methoxy-4-methyl-2,6-dipropoxycyclohexa-2,5-dien-1-one Chemical compound CCCOC1=CC(C)(OC)C=C(OCCC)C1=O VUFGBBBKZZPLKV-UHFFFAOYSA-N 0.000 description 1
- ALGMNKPNZXANDI-UHFFFAOYSA-N 4-methyl-2,4,6-tripropoxycyclohexa-2,5-dien-1-one Chemical compound CCCOC1=CC(C)(OCCC)C=C(OCCC)C1=O ALGMNKPNZXANDI-UHFFFAOYSA-N 0.000 description 1
- IGOWLGAXJASRRI-UHFFFAOYSA-N 4-methylidene-2,6-dipropoxycyclohexa-2,5-dien-1-one Chemical compound CCCOC1=CC(=C)C=C(OCCC)C1=O IGOWLGAXJASRRI-UHFFFAOYSA-N 0.000 description 1
- XOUSBEKUMOSQRO-UHFFFAOYSA-N 6-ethoxy-1,5,6-trimethoxy-3-methylidenecyclohexa-1,4-diene Chemical compound CCOC1(OC)C(OC)=CC(=C)C=C1OC XOUSBEKUMOSQRO-UHFFFAOYSA-N 0.000 description 1
- RPNYEZDNVKGMBO-UHFFFAOYSA-N 6-methoxy-3-methylidene-1,5,6-tripropoxycyclohexa-1,4-diene Chemical compound CCCOC1=CC(=C)C=C(OCCC)C1(OC)OCCC RPNYEZDNVKGMBO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61026552A JPS61178946A (ja) | 1986-02-07 | 1986-02-07 | シクロヘキサジエン誘導体の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61026552A JPS61178946A (ja) | 1986-02-07 | 1986-02-07 | シクロヘキサジエン誘導体の製造法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56027475A Division JPS57140738A (en) | 1980-10-29 | 1981-02-25 | Cyclohexadiene derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61178946A JPS61178946A (ja) | 1986-08-11 |
| JPS6335614B2 true JPS6335614B2 (US20110232667A1-20110929-C00004.png) | 1988-07-15 |
Family
ID=12196684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61026552A Granted JPS61178946A (ja) | 1986-02-07 | 1986-02-07 | シクロヘキサジエン誘導体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61178946A (US20110232667A1-20110929-C00004.png) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02143314U (US20110232667A1-20110929-C00004.png) * | 1989-05-08 | 1990-12-05 |
-
1986
- 1986-02-07 JP JP61026552A patent/JPS61178946A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02143314U (US20110232667A1-20110929-C00004.png) * | 1989-05-08 | 1990-12-05 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61178946A (ja) | 1986-08-11 |
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