GB702112A - Pyran derivatives and process for the manufacture thereof - Google Patents
Pyran derivatives and process for the manufacture thereofInfo
- Publication number
- GB702112A GB702112A GB11653/52A GB1165352A GB702112A GB 702112 A GB702112 A GB 702112A GB 11653/52 A GB11653/52 A GB 11653/52A GB 1165352 A GB1165352 A GB 1165352A GB 702112 A GB702112 A GB 702112A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- capronyl
- dimethyl
- pentyl
- ester
- 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
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0702112/IV(b)/1> wherein R is a branched chain saturated or unsaturated aliphatic hydrocarbon radical containing more than 5 carbon atoms. They are produced by heating an acetoacetic acid ester homologue of the formula R.CO.CH2.COOR1 (wherein R1 is an alkyl radical containing from one to three carbon atoms in the presence of an alkaline catalyst at 180 DEG -220 DEG C. and distilling off the alcohol formed during the reaction. Sodium bicarbonate is the preferred catalyst. The products have antibacterial action. In example (1) (a -methyl-capronyl)-acetic acid methyl ester is heated at 200 DEG -215 DEG C. with sodium bicarbonate while distilling off methyl alcohol, there being produced 3-(a -methyl-capronyl) - 6 - (a - methyl - pentyl) - 2, 3 - dihydro-pyran-2, 4- dione. From the appropriately substituted acetoacetic acid esters there are produced in a similar manner pyran derivatives of the above general formula where R represents (2) b -methyl-pentyl; (3) b , d -dimethyl-pentyl; (4) d -methyl-pentyl; (5) a , d -dimethyl-pentyl; (6) a , g -dimethyl-butyl; (7) b -ethyl-pentyl; (8) b , b -dimethyl-butyl; (9) b -propyl-pentyl; (10 phytyl-methyl; (11); a -ethyl-pentyl. a -(Methyl-capronyl)-acetic acid methyl ester is obtained by reacting a -methyl-capronyl chloride (produced by reacting a -methyl caproic acid and phosphorus trichloride) with sodio-acetoacetic acid methyl ester and treating the product with a solution of sodium in methanol. From the appropriate carboxylic acid (after conversion to its acid chloride) and sodio-acetoacetic acid methyl ester there are prepared compounds of formula R.CO.CH2.COOCH3 where R.CO is a b -methyl-capronyl-, b , d -dimethyl capronyl, d -methyl-capronyl, a , d -dimethyl-capronyl-, a , d -dimethyl-valeryl-, b -ethyl-capronyl-, b , b -dimethyl-valeryl-, b -propyl-capronyl-, phytyl-methyl-, or a -ethyl capronyl radical. Phytyl-acetic acid is prepared by reacting phytyl bromide with sodio-malonic acid ester and saponifying and decarboxylating the phytyl-malonic ester formed. b , b -dimethyl-valeric acid is obtained by reacting malonic acid diethyl ester with 2-bromo-2-methyl-butane and hydrolyzing and decarboxylating the ester formed.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH702112X | 1951-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB702112A true GB702112A (en) | 1954-01-06 |
Family
ID=4530120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11653/52A Expired GB702112A (en) | 1951-05-29 | 1952-05-08 | Pyran derivatives and process for the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB702112A (en) |
-
1952
- 1952-05-08 GB GB11653/52A patent/GB702112A/en not_active Expired
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