GB873455A - Process for the preparation of ª+-ketonic carboxylic acids - Google Patents
Process for the preparation of ª+-ketonic carboxylic acidsInfo
- Publication number
- GB873455A GB873455A GB7391/59A GB739159A GB873455A GB 873455 A GB873455 A GB 873455A GB 7391/59 A GB7391/59 A GB 7391/59A GB 739159 A GB739159 A GB 739159A GB 873455 A GB873455 A GB 873455A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- chloride
- hydroxy
- reacting
- preparation
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
e -Ketonic carboxylic acids and salts thereof are prepared by reacting an adipic acid dialkyl ester with an alkali metal by the Dieckmann condensation to form an alkali metal derivative of a 2-ketocyclopentane carboxylic acid ester, reacting this with an acid halide RCOX (where R is an aliphatic branched or unbranched radical which may be substituted, and X is halogen) and reacting the resulting compound with an alkaline saponification agent to effect saponification, ring opening and partial decarboxylation to yield a salt of the desired acid which may then be converted to the free acid. The Dieckmann condensation is preferably effected in an inert solvent, the alcohol formed being distilled off simultaneously, and the acid halide added to the residue. The acid halide may contain a functional group which may or may not be protected, e.g. protected hydroxy, protected carboxyl or halogen, or a double bond. Examples describe the preparation of: (1) 6-ketohexadecenoic - 15 - acid using undecenyl - 10 - oyl chloride; (2) 6-ketononanoic acid using butyric chloride; (3) 8-methyl-6-ketononanoic acid using isovaleric bromide; (4) 6-ketotricosanoic acid using stearoyl chloride; (5) 15-hydroxy-6-ketopentadecanoic acid using 10-acetoxy-decanoyl chloride; (6) 16-hydroxy-6-ketohexadecanoic acid using 11-bromoundecanoyl chloride; and (7) 5-ketotetradecanedicarboxylic acid-1,14 using 9-ethoxycarboxyl-nonanoyl chloride. The sodium and potassium derivatives of 2-ketocyclopentane carboxylic acid ethyl ester are prepared as intermediates from diethyl adipate by the Dieckmann condensation. Reference is made to the preparation of penta- and hexa-decanolides by the WolffKisbuer reduction and subsequent lactonisation of 15-hydroxy-6-ketopentadecanoic and 16-hydroxy-6-ketohexadecanoic acids respectively and of cyclopentadecanone by acyloin ring closure and reduction of 5-keto-tetra-decanedicarboxylic acid-1,14. Specifications 748,801 and 803,120 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL873455X | 1958-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB873455A true GB873455A (en) | 1961-07-26 |
Family
ID=19851292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7391/59A Expired GB873455A (en) | 1958-03-11 | 1959-03-03 | Process for the preparation of ª+-ketonic carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB873455A (en) |
-
1959
- 1959-03-03 GB GB7391/59A patent/GB873455A/en not_active Expired
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