JPS5587738A - Preparation of cyclohexene derivative - Google Patents
Preparation of cyclohexene derivativeInfo
- Publication number
- JPS5587738A JPS5587738A JP16345978A JP16345978A JPS5587738A JP S5587738 A JPS5587738 A JP S5587738A JP 16345978 A JP16345978 A JP 16345978A JP 16345978 A JP16345978 A JP 16345978A JP S5587738 A JPS5587738 A JP S5587738A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- action
- myrcenol
- cyclohexene
- derivative
- 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.)
- Pending
Links
- 125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 title abstract 2
- 239000002841 Lewis acid Substances 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 150000007517 lewis acids Chemical class 0.000 abstract 2
- DUNCVNHORHNONW-UHFFFAOYSA-N myrcenol Chemical compound CC(C)(O)CCCC(=C)C=C DUNCVNHORHNONW-UHFFFAOYSA-N 0.000 abstract 2
- 229930008383 myrcenol Natural products 0.000 abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 230000003356 anti-rheumatic effect Effects 0.000 abstract 1
- 230000000767 anti-ulcer Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- ALZKKFQIDAVASU-UHFFFAOYSA-N methyl 4-(4-hydroxy-4-methylpentyl)-1-methylcyclohex-3-ene-1-carboxylate Chemical compound COC(=O)C1(C)CCC(CCCC(C)(C)O)=CC1 ALZKKFQIDAVASU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To prepare a highly pure cyclohexene derivative having pharmaceutical actions, e.g. antiallergic action, antiulcer action, antirheumatic action, etc., safely, in high yield in a shortened process, by reacting a methacrylic acid derivative with myrcenol in the presence of a Lewis acid.
CONSTITUTION: A compound II (R is carboxyl, lower alkoxycarbonyl, formyl or cyano) (e.g. methyl methacrylate, etc.) is reacted with myrcenol I in the presence of a Lewis acid MXn (M is amphoteric metal; X is halogen; n is 3W4) (e.g. aluminum chloride, etc.; 0.01W0.5mol on the basis of 1mol of the reactant) to give the desired compound III, e.g. methyl 1-methyl-4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxylate, etc.
EFFECT: It can be industrially produced in a large scale.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16345978A JPS5587738A (en) | 1978-12-26 | 1978-12-26 | Preparation of cyclohexene derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16345978A JPS5587738A (en) | 1978-12-26 | 1978-12-26 | Preparation of cyclohexene derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5587738A true JPS5587738A (en) | 1980-07-02 |
Family
ID=15774276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16345978A Pending JPS5587738A (en) | 1978-12-26 | 1978-12-26 | Preparation of cyclohexene derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5587738A (en) |
-
1978
- 1978-12-26 JP JP16345978A patent/JPS5587738A/en active Pending
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