GB804089A - Process for the preparation of cyclohexanone derivatives - Google Patents
Process for the preparation of cyclohexanone derivativesInfo
- Publication number
- GB804089A GB804089A GB1832/57A GB183257A GB804089A GB 804089 A GB804089 A GB 804089A GB 1832/57 A GB1832/57 A GB 1832/57A GB 183257 A GB183257 A GB 183257A GB 804089 A GB804089 A GB 804089A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ene
- cyclohex
- general formula
- vinyl
- magnesium
- 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
- 238000000034 method Methods 0.000 title abstract 4
- JHIVVAPYMSGYDF-PTQBSOBMSA-N cyclohexanone Chemical class O=[13C]1CCCCC1 JHIVVAPYMSGYDF-PTQBSOBMSA-N 0.000 title 1
- -1 alkyl radicals Chemical class 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 abstract 2
- MUNUMTIUQUUXET-UHFFFAOYSA-N 1-methyl-2-(2-methylpropoxy)cyclohexene Chemical compound CC=1CCCCC=1OCC(C)C MUNUMTIUQUUXET-UHFFFAOYSA-N 0.000 abstract 1
- FKJAZODXPHIGOL-UHFFFAOYSA-N 3-(2-methylpropoxy)cyclohex-2-en-1-one Chemical compound CC(C)COC1=CC(=O)CCC1 FKJAZODXPHIGOL-UHFFFAOYSA-N 0.000 abstract 1
- QAICGYMUDJMDBB-UHFFFAOYSA-N 3-ethenyl-2-methylcyclohex-2-en-1-one Chemical compound CC1=C(C=C)CCCC1=O QAICGYMUDJMDBB-UHFFFAOYSA-N 0.000 abstract 1
- SYSKKMBZQQKRKI-UHFFFAOYSA-N 3-ethenylcyclohex-2-en-1-one Chemical compound C=CC1=CC(=O)CCC1 SYSKKMBZQQKRKI-UHFFFAOYSA-N 0.000 abstract 1
- DCXVEXOSXDDABX-UHFFFAOYSA-N 3-prop-1-enylcyclohex-2-en-1-one Chemical compound CC=CC1=CC(=O)CCC1 DCXVEXOSXDDABX-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 150000002680 magnesium Chemical class 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0804089/IV (b)/1> wherein R2 and R3 are hydrogen atoms, lower alkyl radicals containing at most four carbon atoms or aryl radicals and a process for the preparation of compounds of the general formula <FORM:0804089/IV (b)/2> wherein R represents a hydrogen atom or a lower alkyl radical as defined above and R1, R2 and R3 represent hydrogen atoms, lower alkyl radicals as defined above or aryl radicals which comprises reacting an enolic ether of the general formula <FORM:0804089/IV (b)/3> in which R1 represents a lower aliphatic hydrocarbon radical containing from 3 to 5 carbon atoms and R has the significance set forth, with an alk-1-enyl-magnesium halide of the general formula <FORM:0804089/IV (b)/4> wherein X represents a chlorine or bromine atom and the radicals R1, R2 and R3 have the significances set forth and decomposing the magnesium derivative formed by treatment with a dilute mineral acid. In examples: 2-methyl - 3 - vinylcyclohex - 2 - ene - 1 - one is obtained by treating 2-methyl-3-isobutoxy-cyclohex - 2 - ene - 1 one with vinyl magnesium bromide, prepared by reacting magnesium with vinyl bromide in tetrahydrofuran and adding excess dilute sulphuric acid to the reaction product (I); 3-vinyl-cyclohex-2-ene-1-one is obtained by reacting vinyl magnesium bromide and 3-isobutoxy-cyclohex-2-ene-1-one in a similar process (II). Other compounds made by analogous processes are 3-(1-propenyl) cyclohex-2-ene-1-one, 3-(1-isocrotyl) cyclohex - 2 - ene - 1 - one and 3 - (1 - a - methyl-styryl)-cyclohex-2-ene-1-one.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR804089X | 1956-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB804089A true GB804089A (en) | 1958-11-05 |
Family
ID=9250532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1832/57A Expired GB804089A (en) | 1956-02-01 | 1957-01-17 | Process for the preparation of cyclohexanone derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB804089A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3431305A (en) * | 1965-02-08 | 1969-03-04 | Eastman Kodak Co | Process for the production of 2-(propenyl)-2-cyclohexenone |
-
1957
- 1957-01-17 GB GB1832/57A patent/GB804089A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3431305A (en) * | 1965-02-08 | 1969-03-04 | Eastman Kodak Co | Process for the production of 2-(propenyl)-2-cyclohexenone |
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