GB824610A - Process for the preparation of unsaturated organomagnesium halides - Google Patents
Process for the preparation of unsaturated organomagnesium halidesInfo
- Publication number
- GB824610A GB824610A GB8540/58A GB854058A GB824610A GB 824610 A GB824610 A GB 824610A GB 8540/58 A GB8540/58 A GB 8540/58A GB 854058 A GB854058 A GB 854058A GB 824610 A GB824610 A GB 824610A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ether
- halogen
- carbinol
- derivative
- 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
- -1 unsaturated organomagnesium halides Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 8
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 239000002904 solvent Substances 0.000 abstract 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 239000002202 Polyethylene glycol Substances 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- GQKZBCPTCWJTAS-UHFFFAOYSA-N methoxymethylbenzene Chemical compound COCC1=CC=CC=C1 GQKZBCPTCWJTAS-UHFFFAOYSA-N 0.000 abstract 2
- 229920001223 polyethylene glycol Polymers 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- NNQDMQVWOWCVEM-NSCUHMNNSA-N (e)-1-bromoprop-1-ene Chemical compound C\C=C\Br NNQDMQVWOWCVEM-NSCUHMNNSA-N 0.000 abstract 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 1
- ZQAYBCWERYRAMF-UHFFFAOYSA-N 1-methoxy-3-methylbutane Chemical compound COCCC(C)C ZQAYBCWERYRAMF-UHFFFAOYSA-N 0.000 abstract 1
- HGUIQUVFOYTZNC-UHFFFAOYSA-N 1-phenylhex-1-yn-3-ol Chemical compound CCCC(O)C#CC1=CC=CC=C1 HGUIQUVFOYTZNC-UHFFFAOYSA-N 0.000 abstract 1
- RMGHERXMTMUMMV-UHFFFAOYSA-N 2-methoxypropane Chemical compound COC(C)C RMGHERXMTMUMMV-UHFFFAOYSA-N 0.000 abstract 1
- OWVUFBAJXKEVBE-UHFFFAOYSA-N 2-methylpent-3-en-2-ol Chemical compound CC=CC(C)(C)O OWVUFBAJXKEVBE-UHFFFAOYSA-N 0.000 abstract 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- XJMAJAGAHDFDLE-UHFFFAOYSA-N dec-2-en-4-ol Chemical compound CCCCCCC(O)C=CC XJMAJAGAHDFDLE-UHFFFAOYSA-N 0.000 abstract 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- RRRODBVLAIUQDT-UHFFFAOYSA-N oct-3-yn-2-ol Chemical compound CCCCC#CC(C)O RRRODBVLAIUQDT-UHFFFAOYSA-N 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Organomagnesium halides may be prepared by reacting magnesium with a halogen derivative of an unsaturated organic compound in an inert atmosphere, the reaction being initiated with a small portion of the said halogen derivative in a primary solvent medium comprising tetrahydrofuran, tetrahydropyran, an alkyl derivative of either or a polyethylene glycol diether, the primary solvent being then replaced by or mixed with a secondary solvent comprising an aliphatic monoether, a phenolic ether or a formal and the reaction continued with the addition of the remainder of said halogen derivative. The halogen derivative may be of formula <FORM:0824610/IV (b)/1> where X is halogen and the double bond is in a chain or in a homocyclic ring, or of formula R-CC-X, where X is halogen and R is an aliphatic or cyclic radical. Preferred polyethylene glycol diethers are those of formula R1(OCH2CH2)n-O-R2, where R1 and R2 are the same or different and are C2-4 alkyl, and n is 2 or 3. The reaction may be carried out in an atmosphere of nitrogen, and as in conventional Grignard synthetic procedures the product may be reacted to form carbinols, hydrocarbons, &c. Example 1 describes the preparation of the Grignard reagent of 1-bromo-propene using as the primary solvent tetrahydrofuran and as the secondary solvent (a) diethyl ether, (b) methyl iso-amyl ether; (c) methyl benzyl ether; (d) methyl iso-propyl ether; (e) di-n-butyl ether; (f) di-isopropyl ether; (g) methylal; and (h) a mixture of anisole and diethyl ether. The undermentioned compounds are prepared from the unsaturated organomagnesium halides:- Example 1, hexyl 1-propenyl carbinol, dimethyl 1-propenyl carbinol; Example 2: C2H5O-CH2-CH=CH-CHOH-C6H13 <FORM:0824610/IV (b)/2> Example 3: C7H15CHOH-CH=CH-CH3 <FORM:0824610/IV (b)/3> Benzene, naphthalene. (CH3)2CH-C6H4-CH2.CH=CH2 <FORM:0824610/IV (b)/4> Examples 4, 5-7, methyl-(1-hexynyl)-carbinol. Examples 6, 8, propyl-(2-phenyl-1-ethynyl)-carbinol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR824610X | 1957-04-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB824610A true GB824610A (en) | 1959-12-02 |
Family
ID=9281900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8540/58A Expired GB824610A (en) | 1957-04-26 | 1958-03-17 | Process for the preparation of unsaturated organomagnesium halides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB824610A (en) |
-
1958
- 1958-03-17 GB GB8540/58A patent/GB824610A/en not_active Expired
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