GB626712A - Preparation of crotonic acid derivatives and of phenanthrene derivatives therefrom - Google Patents
Preparation of crotonic acid derivatives and of phenanthrene derivatives therefromInfo
- Publication number
- GB626712A GB626712A GB24205/46A GB2420546A GB626712A GB 626712 A GB626712 A GB 626712A GB 24205/46 A GB24205/46 A GB 24205/46A GB 2420546 A GB2420546 A GB 2420546A GB 626712 A GB626712 A GB 626712A
- Authority
- GB
- United Kingdom
- Prior art keywords
- side chain
- product
- closed
- keto
- heated
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Tetrahydro naphthylidene derivatives of crotonic acid are made by reacting a 1-keto-tetrahydronaphthylene with a g -halogen crotonic ester under the conditions of the Reformatsky reaction, and the ester produced is hydrolysed to the free acid. The 1-keto-tetrahydronaphthylenes have the general formula <FORM:0626712/IV (b)/1> in which R is alkoxy, aryloxy, hydroxy or hydrogen. The product may be isomerized by heating with palladium to form a naphthalene acid derivative with a saturated side chain, and the side chain closed by known methods to form a ring. Alternatively, the product may be reduced to form a saturated side chain structure, heated with sulphur to produce a naphthalenic derivative and the side chain then closed to form a ring structure. In an example, g -bromocrotonic ester is added to a mixture of zinc wool, dry benzene, mercuric chloride and 6-methoxy-1-tetralone, the product isolated by acidifying and extracting with ether, and hydrolysed with potassium hydroxide in aqueous methanol. The product has the formula <FORM:0626712/IV (b)/2> In a second example, this product is heated with palladium black to give the isomeric naphthalene derivative having a saturated side chain, and the side chain is converted to a closed ring in known manner to yield 7-methoxy-1-keto-1,2,3,4-tetrahydrophenanthrene. In a third example, the acid produced in the first example is reduced with hydrogen in presence of Raney nickel and the product heated with sulphur and the side chain closed to give the same product as in the previous example.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24205/46A GB626712A (en) | 1946-08-14 | 1946-08-14 | Preparation of crotonic acid derivatives and of phenanthrene derivatives therefrom |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24205/46A GB626712A (en) | 1946-08-14 | 1946-08-14 | Preparation of crotonic acid derivatives and of phenanthrene derivatives therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB626712A true GB626712A (en) | 1949-07-20 |
Family
ID=10208037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24205/46A Expired GB626712A (en) | 1946-08-14 | 1946-08-14 | Preparation of crotonic acid derivatives and of phenanthrene derivatives therefrom |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB626712A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114349631A (en) * | 2022-01-14 | 2022-04-15 | 北京富盛嘉华医药科技有限公司 | Preparation method and application of 4-methoxy crotonic acid |
-
1946
- 1946-08-14 GB GB24205/46A patent/GB626712A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114349631A (en) * | 2022-01-14 | 2022-04-15 | 北京富盛嘉华医药科技有限公司 | Preparation method and application of 4-methoxy crotonic acid |
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