GB1119061A - A process for the production of ª‡,ª‡'-tetrasubstituted ª‡-mononitrile-ª‡'-monocarboxylic acid dimethyl ethers - Google Patents
A process for the production of ª‡,ª‡'-tetrasubstituted ª‡-mononitrile-ª‡'-monocarboxylic acid dimethyl ethersInfo
- Publication number
- GB1119061A GB1119061A GB2439065A GB2439065A GB1119061A GB 1119061 A GB1119061 A GB 1119061A GB 2439065 A GB2439065 A GB 2439065A GB 2439065 A GB2439065 A GB 2439065A GB 1119061 A GB1119061 A GB 1119061A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pict
- prepared
- formula
- compounds
- cooh
- 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- 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
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
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
Compounds containing the grouping <PICT:1119061/C2/1> wherein R1, R2, R3 and R4 represent alkyl, aryl or alkenyl groups, are prepared by fission of the bond between the 3- and 4-carbon atoms in a 2,2,5,5-tetrasubstituted-3-hydroximino-4-oxotetrahydrofuran of the formula <PICT:1119061/C2/2> The final nature of the product is governed by the nature of the fission reaction. Thus (1) compounds of the formula <PICT:1119061/C2/3> wherein Z1 represents a COOH or metal carboxylate group are prepared by heating the furan derivative with water, an alcohol or an inert organic solvent inert to -CN and -COOH groups and boiling above 75 DEG C., at a temperature of from 40 DEG to 200 DEG C. in the presence of a substantially equimolar quantity of an alkali or alkaline earth metal hydroxide, oxide or alkoxide catalyst until the start of evolution of ammonia. (2) Compounds of the formula <PICT:1119061/C2/4> wherein Z and Z1 each represent a -COOH or metal carboxylate group, are prepared by continuing reaction (1) until the cessation of evolution of ammonia. (3) Compounds of the formula <PICT:1119061/C2/5> are prepared by heating the furan derivative in the absence of a catalyst or in the presence of a substantially less than equimolar quantity of an appropriate hydrolysis, esterification or transesterification catalyst at a temperature of from 40 DEG to 200 DEG C. in the presence of water, an alcohol or an organic solvent inert to -COOH and -CN groups and boiling above 75 DEG C. (4) Compounds of the formula <PICT:1119061/C2/6> wherein Y represents an alkyl group, are prepared by carrying out reaction (3) in the presence of an excess of an alcohol of the formula Y-OH. (5) Compounds of the formula <PICT:1119061/C2/7> are prepared by heating the furan derivative at a temperature of from 40 DEG to 200 DEG C. in the presence of an anhydride-forming compound. Products of process (1) may be esterified by reacting the corresponding potassium salt with excess dimethyl sulphate in aqueous benzene. Products of processes (3) and (4), e.g. diisopropyl ether a ,a 1-dicarboxylic acid amide and N-n-butylamide, may be converted by hydrolysis with concentrated hydrochloric acid into the corresponding a -hydroxycarboxylic acids, e.g. a -hydroxyisobutyric acid. 2,2,5,5 - Tetramethyl - 3 - nitroso - 4 - oxotetrahydrofuran is prepared by reacting 2,2,5,5-tetramethyl-4-oxotetrahydrofuran with amyl nitrite. The product is converted to the 3-hydroximino form by addition of sodium hydroxide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH769964A CH435237A (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of dimethyl ether-a, a'-tetrasubstituted-a-mononitrile-a'-monocarboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1119061A true GB1119061A (en) | 1968-07-03 |
Family
ID=4329193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2439065A Expired GB1119061A (en) | 1964-06-12 | 1965-06-09 | A process for the production of ª‡,ª‡'-tetrasubstituted ª‡-mononitrile-ª‡'-monocarboxylic acid dimethyl ethers |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE665312A (en) |
| CH (1) | CH435237A (en) |
| DE (1) | DE1276021B (en) |
| FR (1) | FR1436510A (en) |
| GB (1) | GB1119061A (en) |
| NL (1) | NL6507494A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110981718B (en) * | 2019-12-04 | 2022-08-05 | 万华化学集团股份有限公司 | Method for preparing 3-hydroxypropionic acid by continuous hydration of acrylic acid |
-
1964
- 1964-06-12 CH CH769964A patent/CH435237A/en unknown
-
1965
- 1965-05-31 DE DEL50820A patent/DE1276021B/en active Pending
- 1965-06-09 GB GB2439065A patent/GB1119061A/en not_active Expired
- 1965-06-11 FR FR20511A patent/FR1436510A/en not_active Expired
- 1965-06-11 BE BE665312D patent/BE665312A/xx unknown
- 1965-06-11 NL NL6507494A patent/NL6507494A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE665312A (en) | 1965-10-01 |
| FR1436510A (en) | 1966-04-22 |
| DE1276021B (en) | 1968-08-29 |
| NL6507494A (en) | 1965-12-13 |
| CH435237A (en) | 1967-05-15 |
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