GB603422A - Process for the hydrolysis of 2, 5-dihydrofurans - Google Patents
Process for the hydrolysis of 2, 5-dihydrofuransInfo
- Publication number
- GB603422A GB603422A GB2770245A GB2770245A GB603422A GB 603422 A GB603422 A GB 603422A GB 2770245 A GB2770245 A GB 2770245A GB 2770245 A GB2770245 A GB 2770245A GB 603422 A GB603422 A GB 603422A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dihydrofuran
- dimethoxy
- general formula
- groups
- represent
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Unsaturated dicarbonyl compounds of the general formula R1CO.CH=CHCOR2, where R1 and R2 represent hydrogen, alkyl and carboxylic ester groups, are prepared by hydrolysing, in aqueous medium, 2 : 5-dihydrofurans of the general formula <FORM:0603422/IV(b)/1> where R1 and R2 have the above significance and R3 and R4 represent saturated or unsaturated aliphatic, alicyclic or aliphatic-alicyclic groups, e.g. groups containing up to ten carbon atoms or, preferably, alkyl groups containing up to four carbon atoms. The hydrolysis may be effected either while cooling the reaction mixture or at atmospheric temperature. An acid, e.g. a non-oxidizing acid such as hydrochloric acid, may be present during the reaction, if necessary at a low concentration. The unsaturated dicarbonyl compound may be separated by extracting the reaction medium with an organic solvent, drying the extract, distilling off the solvent and fractionally distilling the residue. Compounds of the general formula <FORM:0603422/IV(b)/2> where R1, R2, R3 and R4 have the significance already indicated, are stated to be formed as intermediate products. In examples: (1) maleic dialdehyde is prepared by shaking water and 2 : 5 - dimethoxy - 2 : 5 - dihydrofuran; (2) 2 : 5 - dimethoxy - 2 : 5 - dihydrofuran, water and hydrochloric acid are shaken, extracted with ether, the extract dried, the ether removed by distillation and the residue fractionated to yield maleic dialdehyde. The preparation of the following dicarbonyl compounds is also mentioned: maleic dialdehyde from 2 : 5-dicyclohexyloxy - 2 : 5 - dihydrofuran or 2 : 5 - diallyloxy - 2 : 5 - dihydrofuran, b -acetylacrolein from 2 : 5 - dimethoxy - 2 : 5 - dihydrosylvan, a b -diacetyl ethylene from 2 : 5-dimethyl-2 : 5-dimethoxy-2 : 5-dihydrofuran, and (21-formylvinyl) - 1 - keto - acetic methyl ester from 2 : 5 - dimethoxy-2 : 5-dihydromethylfuroate-2. The Provisional Specification refers also to the preparation of dicarbonyl compounds of the above general formula, where in addition R1 and R2 represent alkoxy and carboxylic groups, by the hydrolysis of 2 : 5-dihydrofurans of the above general formula, where in addition R3 and R4 represent aromatic or substituted aromatic groups.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2770245A GB603422A (en) | 1945-10-22 | 1945-10-22 | Process for the hydrolysis of 2, 5-dihydrofurans |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2770245A GB603422A (en) | 1945-10-22 | 1945-10-22 | Process for the hydrolysis of 2, 5-dihydrofurans |
Publications (1)
Publication Number | Publication Date |
---|---|
GB603422A true GB603422A (en) | 1948-06-15 |
Family
ID=10263902
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2770245A Expired GB603422A (en) | 1945-10-22 | 1945-10-22 | Process for the hydrolysis of 2, 5-dihydrofurans |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB603422A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4384144A (en) * | 1976-04-05 | 1983-05-17 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing cyclopentenone derivatives |
-
1945
- 1945-10-22 GB GB2770245A patent/GB603422A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4384144A (en) * | 1976-04-05 | 1983-05-17 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing cyclopentenone derivatives |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Shi et al. | A novel and versatile access to fluorinated carbo-and heterocyclic compounds employing electron-rich fluorodienes as cycloaddition components | |
Nieuwenhuis et al. | Chemistry of acetylenic ethers XXXII. Formation of 1, 3‐dialkyl‐2‐ethoxy‐cyclobut‐2‐ene‐4‐ones from ethyl 1‐alkynyl ethers | |
GB603422A (en) | Process for the hydrolysis of 2, 5-dihydrofurans | |
Ingham et al. | A synthesis of freelingyne | |
US4360691A (en) | Production of malonic anhydrides and derivatives thereof | |
US3349130A (en) | Novel process for the preparation of 2-alkyl-cyclopentane-1, 3-diones | |
GB815279A (en) | Novel benzomorpholone derivatives and a process for the manufacture thereof | |
US2772295A (en) | Process of manufacturing esters of 3-substituted 2-furoic acids | |
US2599549A (en) | Production of alpha-carbalkoxyalkyl methacrylates | |
US3700694A (en) | Insect control | |
US2453677A (en) | Alkamine esters of pyrrole-3, 4-dicarboxylic acids | |
US2209092A (en) | Thiazole compound and process of preparing the same | |
US2140480A (en) | 3-keto-d-pentonic acid lactone and process for the manufacture of same | |
GB788541A (en) | 3, 4-epoxycyclohexanecarboxylic acids and esters thereof | |
US3780087A (en) | Glycolates from acetals | |
SU76328A1 (en) | Method for preparing diacyl acetic esters and C-acylphenols | |
US2523692A (en) | Ester condensation | |
GB751035A (en) | Improvements in and relating to the condensation of dialkyl succinates | |
JPS6311351B2 (en) | ||
SU125567A1 (en) | Method for preparing vinylpyrrolidone | |
GB588377A (en) | Improvements in and relating to the production of furan derivatives | |
DE809806C (en) | Process for the preparation of unsaturated dicarbonyl compounds | |
SU429059A1 (en) | METHOD OF OBTAINING DERIVATIVES \ - | |
Hayes | Chemotherapeutic Nitrofurans. III. 1 N-(5-Nitro-2-furfurylidene)-3-aminotetrahydro-1, 3-oxazine-2-one | |
CH509957A (en) | Thermal rearrangement of allyl vinylethers |