CS245189B1 - Preparation of 1- (2,6-dimethylphenoxy) -2-propanone - Google Patents
Preparation of 1- (2,6-dimethylphenoxy) -2-propanone Download PDFInfo
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- CS245189B1 CS245189B1 CS848176A CS817684A CS245189B1 CS 245189 B1 CS245189 B1 CS 245189B1 CS 848176 A CS848176 A CS 848176A CS 817684 A CS817684 A CS 817684A CS 245189 B1 CS245189 B1 CS 245189B1
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Abstract
Spósob přípravy l-/2,6-dimetylfenoxy/- -2-propanónu z 2,6-dimetylfenolu, chlóracetonu a jódu za přítomnosti slabej anorganickéj alebo organickéj kyseliny, ktorý sa používá ako medziprodukt pri výrobě liečiv vo farmaceutickom priemysleMethod for the preparation of 1-/2,6-dimethylphenoxy/- -2-propanone from 2,6-dimethylphenol, chloroacetone and iodine in the presence of a weak inorganic or organic acid, which is used as an intermediate in the production of drugs in the pharmaceutical industry
Description
245189 2
Vynález sa týká spósobu přípravy l-/2,6-dimetylfenoxy/-2-propanónu vzorca I
o-ch2-co-ch3 ch3 ktorý sa používá ako medziprodukt pri výrobě liečiv.
Doposial sa táto zlúčenina vyrábala z 2,6-dimetylfenolu a brómacetónu za přítomnostiuhličitanu draselného v prostředí acetonu s výtažkom 27 až 37 * /D. S. Tarbell: J. Org.
Chem. 7. 251 /1942//. Druhou popísanou metodou přípravy zlúčeniny I je oxidácia L-/2,6--dimetylfenoxy/-2-propanolu róznymi oxidačnými činidlami /D. Hesek a spol.: Csl. AO 223436/1983//.
Spósob přípravy zlúčeniny I je založený na reakci! 1 mol. dielu 2,6-dimetylfenolus 1,0 až 1,5 mol. dielom chloracetonu a 0,005 až 0,1 mol. dielom jódu za přítomnosti 0,5až 1,5 mol. dielu alkalickej soli slabej anorganickej alebo organickej kyseliny v prostředíorganického rozpúšíadla pri teplote 40 °C až teplote varu použitého rozpúšťadla.
Ako alkalické sol slabej anorganickej alebo organickej kyseliny možno použit uhličitany/hydrogénuhličitan sodný, uhličitan sodný alebo draselný/, připadne octany /octan sodnýalebo draselný/.
Ako organické rozpúšťadlo možno použit alifatické alkoholy s počtom uhlíkov 1 až 4, napr.metanol, etanol, 2-propanol, n.butanol, 2-metylpropanol, alebo alifatické ketony s počtomuhlíkov 3 až 6, napr. aceton, metyl-etyl-keton, metyl-terc. butylketon. Je výhodné použitbezvodé rozpúšťadlá s maxímálnym obsahom 0,1 % vody.
Postup podlá vynálezu sa uskutočftuje tak, že k zmesi 2,6-dimetylfenolu, jódu a alkalic-kej soli slabej anorganickej alebo organickej kyseliny v organickom rozpúštadle vyhriatejminimálně na teplotu 40 °C až teplotu varu organického rozpúšťadla sa za mlešania přidávápo častiach chloraceton a na doreagovanie sa ohrieva na teplotu spíitného varu po dobu 5 až20 hod. Pri víičších návažkach je vhodné.přidávat chloraceton zriedený použitým organickýmrozpúšťadlom.
Izolácia zlúčeniny I sa uskutočňuje tak, že sa k reakčnej zmesi najprv odseparujú anor-ganické soli odsátím alebo odfiltrováním na tlakovom filtri a získaný filtrát sa vákuovodestiluje.
Hlavnou. výhodou postupu podlá vynálezu oproti prvej z popísaných metod přípravy zlúčeninyI je dosiahnutie podstatné vyšších výťažkov. Oproti druhej z popísaných metod přípravy zlú-čeniny I má postup podlá vynálezu výhodu v 1-stupftovej, oproti doteraz 2-stupňovej syntéze. V ďalšom je predmet vynálezu popísaný v příklade prevedenia bez toho, že by sa na tentoobmedzoval. Příklad 1 K zmesi 50 g 2,6-dimetylfenolu, 57 g bezvodého uhličitanu draselného a 3 g jódu v 200 mlacetonu, vyhriatej k varu sa za miešania v priebehu 5 min. přidá po malých dávkách 50 gchloracetonu v 50 ml acetonu. Zmes sa zahrieva k varu za neustálého miešania počas 12 hod.Potom sa reakčná zmes ochladí na cca 25 °c, anorganické soli odfiltrujú a premyjú acetonom.Filtrát sa zahustí na rotačnej vákuovej odparke a získaný surový produkt sa vákuovo predesti-luje /88 až 82 °C pri 93 až 135 Pa/. Získá sa cca 69 g 1-/2,6-dimetylfenoxy/-2-propanonuo obsahu cca 94 %, čo představuje výťažok cca 88 %,
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The invention relates to a process for the preparation of 1- (2,6-dimethylphenoxy) -2-propanone of formula I
o-ch2-co-ch3 which is used as an intermediate in the manufacture of medicaments.
To date, this compound has been prepared from 2,6-dimethylphenol and bromoacetone in the presence of potassium carbonate in an acetone medium of 27-37% (DS Tarbell: J. Org.).
Chem. 7. 251 (1942). The second method described for the preparation of compound I is the oxidation of L- (2,6-dimethylphenoxy) -2-propanol with various oxidizing agents / D. Hesek et al .: Csl. AO 223436 (1983).
The method of preparing compound I is based on the reaction! 1 mol. part of 2,6-dimethylphenol 1.0-1.5 mol. chloroacetone and 0.005 to 0.1 mol. iodine in the presence of 0.5 to 1.5 mol. part of an alkali salt of a weak inorganic or organic acid in an organic solvent at 40 ° C to the boiling point of the solvent used.
As the alkali metal salt of a weak inorganic or organic acid, sodium carbonate / sodium bicarbonate, sodium carbonate or potassium carbonate (optionally acetate / sodium acetate or potassium) may be used.
As the organic solvent, aliphatic alcohols having carbon numbers of 1 to 4 may be used, such as methanol, ethanol, 2-propanol, n-butanol, 2-methylpropanol, or aliphatic ketones of from 3 to 6, e.g., acetone, methyl ethyl ketone , methyl tert. butylketone. It is preferred to use anhydrous solvents with a maximum content of 0.1% water.
The process of the invention is carried out by adding to the mixture of 2,6-dimethylphenol, iodine and an alkaline salt of a weak inorganic or organic acid in an organic solvent at least 40 ° C to the boiling point of the organic solvent, while stirring, with chloroacetone and for quenching. is heated to the reflux temperature for 5-20 hours. For more weights, it is suitable to add the chloroacetone diluted with the organic solvent used.
The isolation of Compound I is accomplished by first separating the inorganic salts from the reaction mixture by suction or filtration on a pressure filter and distilling off the filtrate.
Main. the advantage of the process of the invention over the first of the described methods of preparing compound I is to achieve substantial higher yields. In contrast to the other methods of preparing Compound (I) described above, the process of the invention has the advantage of 1-step, as opposed to a 2-step synthesis. In the following, the invention is described in the exemplary embodiment without being limited thereto. Example 1 To a mixture of 50 g of 2,6-dimethylphenol, 57 g of anhydrous potassium carbonate and 3 g of iodine in 200 ml of acetone heated to boiling with stirring for 5 min. 50 g of chloroacetone in 50 ml of acetone are added in small portions. The mixture is heated to boiling with stirring for 12 hours. The reaction mixture is then cooled to about 25 ° C, the inorganic salts are filtered off and washed with acetone. ° C at 93-135 Pa /. Approximately 69 g of 1- (2,6-dimethylphenoxy) -2-propanone is obtained, with a content of about 94%, which represents a yield of about 88%,
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS848176A CS245189B1 (en) | 1984-10-29 | 1984-10-29 | Preparation of 1- (2,6-dimethylphenoxy) -2-propanone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS848176A CS245189B1 (en) | 1984-10-29 | 1984-10-29 | Preparation of 1- (2,6-dimethylphenoxy) -2-propanone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS817684A1 CS817684A1 (en) | 1985-12-16 |
| CS245189B1 true CS245189B1 (en) | 1986-08-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS848176A CS245189B1 (en) | 1984-10-29 | 1984-10-29 | Preparation of 1- (2,6-dimethylphenoxy) -2-propanone |
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| CS (1) | CS245189B1 (en) |
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1984
- 1984-10-29 CS CS848176A patent/CS245189B1/en unknown
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| Publication number | Publication date |
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| CS817684A1 (en) | 1985-12-16 |
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