GB772215A - Process for the production of new di-acylated tartaric acids - Google Patents
Process for the production of new di-acylated tartaric acidsInfo
- Publication number
- GB772215A GB772215A GB18215/55A GB1821555A GB772215A GB 772215 A GB772215 A GB 772215A GB 18215/55 A GB18215/55 A GB 18215/55A GB 1821555 A GB1821555 A GB 1821555A GB 772215 A GB772215 A GB 772215A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tartaric acid
- acid
- carboxylic acid
- tartaric
- coumarine
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises as new products diacylated tartaric acids of the general formula <FORM:0772215/IV(b)/1> <FORM:0772215/IV(b)/2> wherein R is the radical of an a ,b unsaturated aliphatic carboxylic acid or the radical of an a ,b unsaturated carboxylic acid, wherein the a and the b carbon atoms are part of a non-aromatic ring. The preferred products are those in which R is the radical of an a ,b unsaturated aliphatic carboxylic acid which contains not more than 10 carbon atoms, and the radical of an a ,b unsaturated carboxylic acid in which the a and b carbon atoms are part of a non-aromatic six-membered ring, e.g. the radical of an a ,b -unsaturated carboxylic acid in which the a and the b carbon atoms are part of a coumarine ring. The products may be obtained by reacting d or l tartaric acid with the halide of the a -b carboxylic acid and converting any diacyl tartaric acid anhydride produced into the corresponding acid by treatment with a mildly acting hydrolysing agent. In examples: (1) coumarine-3-carboxylic acid chloride and d-tartaric are heated at 135-145 DEG C. in xylene for 3 hours. The mass is then diluted with benzene and cooled to yield a crystalline precipitate which is filtered off and boiled with benzene to extract coumarine-3-carboxylic acid anhydride whilst the benzene insoluble mass containing the anhydride of the desired di-coumarine-3-carboxylic acid ester of d-tartaric acid is shaken out with acetone and then boiled with 90 per cent acetone to hydrolyse the anhydride to di-coumarine-3-carboxylic acid ester of d-tartaric acid; (2) di-coumarine-3-carboxylic acid ester of l-tartaric acid is obtained by a procedure as in (1) except that l-tartaric acid is used; (3) a mixture of crotonic acid chloride and d-tartaric acid is heated to 110-120 DEG C. and then to 140-150 DEG C. to complete the reaction and the excess acid chloride is distilled off. After cooling, the solidified residue is extracted with petroleum ether and the extract cooled to precipitate dicrotonyl-d-tartaric acid anhydride which is then hydrolysed by boiling with 50 per cent acetone to form di-crotonyl-d-tartaric acid; (4) di-crotonyl-l-tartaric acid is obtained by a procedure as in (3) except that l-tartaric acid is used; (5) di - (b b - dimethylacryl) - l - tartaric acid is obtained by heating l-tartaric acid with dimethyl acrylic acid chloride at 110 DEG C. and then at 140 DEG C., cooling, extracting with ligroin, cooling the extract to form a crystalline pulp comprising di-(b b -dimethylacryl)-l-tartaric acid anhydride and hydrolysing the latter by boiling with 94 per cent acetone; (6) di-(b b -dimethylacryl)-d-tartaric acid is obtained by a similar procedure to (5) except that d-tartaric acid is used and 95 per cent acetone is used for the hydrolysis. The products are stated to be suitable for use in the separation of mixtures of lysergic and isolysergic acid derivatives. Specification 573,514, [Group IV], is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH772215X | 1954-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB772215A true GB772215A (en) | 1957-04-10 |
Family
ID=4535505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18215/55A Expired GB772215A (en) | 1954-06-23 | 1955-06-23 | Process for the production of new di-acylated tartaric acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB772215A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002503241A (en) * | 1997-06-03 | 2002-01-29 | サントル・ナショナル・ドゥ・ラ・ルシェルシェ・シャンティフィク | Coumarin derivatives, their production method and their use as pharmaceuticals |
-
1955
- 1955-06-23 GB GB18215/55A patent/GB772215A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002503241A (en) * | 1997-06-03 | 2002-01-29 | サントル・ナショナル・ドゥ・ラ・ルシェルシェ・シャンティフィク | Coumarin derivatives, their production method and their use as pharmaceuticals |
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