GB908504A - Process for the production of new glycols - Google Patents
Process for the production of new glycolsInfo
- Publication number
- GB908504A GB908504A GB22846/59A GB2284659A GB908504A GB 908504 A GB908504 A GB 908504A GB 22846/59 A GB22846/59 A GB 22846/59A GB 2284659 A GB2284659 A GB 2284659A GB 908504 A GB908504 A GB 908504A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- carbon atoms
- ketones
- hydroxy
- radical
- 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
- 150000002334 glycols Chemical class 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- -1 ethinyl methyl carbinols Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/06—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
-
- 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
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention comprises glycols of the general formula <FORM:0908504/IV (b)/1> in which R1 represents an alkyl radical having not more than 6 carbon atoms or a cycloalkyl radical having from 3 to 8 carbon atoms, R2 and R3 represent alkyl radicals having not more than 4 carbon atoms, or R1 and R2 together may form an alkylene radical, and R4 represents an unsaturated aliphatic hydrocarbon radical having 2 or 3 carbon atoms. They may be prepared by reacting, preferably in an organic solvent, an a -hydroxy ketone of general formula <FORM:0908504/IV (b)/2> with an organometallic compound prepared from magnesium or zinc and a compound of formula Hal-CH2-R4, in which Hal represents chlorine, bromine, or iodine, followed by hydrolysis. If desired, compounds in which R4 contains a triple bond may be catalytically hydrogenated to reduce the triple bond to a double bond. The a -hydroxy ketones used as starting materials may be obtained from ketones of formula R1COR2 by converting them to the corresponding cyanohydrins, blocking the hydroxy group, e.g. by acylation, reacting the products with alkyl magnesium halides of formula R3MgHal and hydrolysing the products. Alternatively when R2 and R3 are both methyl groups the starting hydroxy ketones may be obtained by condensing ketones of formula R1COCH3 with alkali metal acetylides and adding water to the ethinyl methyl carbinols so obtained.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6138858A CH367812A (en) | 1958-07-04 | 1958-07-04 | Process for the production of new glycols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB908504A true GB908504A (en) | 1962-10-17 |
Family
ID=4523606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22846/59A Expired GB908504A (en) | 1958-07-04 | 1959-07-03 | Process for the production of new glycols |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH367812A (en) |
| ES (1) | ES250508A1 (en) |
| GB (1) | GB908504A (en) |
-
1958
- 1958-07-04 CH CH6138858A patent/CH367812A/en unknown
-
1959
- 1959-07-03 ES ES0250508A patent/ES250508A1/en not_active Expired
- 1959-07-03 GB GB22846/59A patent/GB908504A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH367812A (en) | 1963-03-15 |
| ES250508A1 (en) | 1960-02-01 |
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