GB978352A - Preparation of 2,2-dichloro-and 2,2-dibromo cyclopropanecarboxylic acids - Google Patents
Preparation of 2,2-dichloro-and 2,2-dibromo cyclopropanecarboxylic acidsInfo
- Publication number
- GB978352A GB978352A GB1057561A GB1057561A GB978352A GB 978352 A GB978352 A GB 978352A GB 1057561 A GB1057561 A GB 1057561A GB 1057561 A GB1057561 A GB 1057561A GB 978352 A GB978352 A GB 978352A
- Authority
- GB
- United Kingdom
- Prior art keywords
- yield
- dichloro
- acid
- dibromo
- sodium
- 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
- ZZQWHIVRLNQEDZ-UHFFFAOYSA-N 2,2-dibromocyclopropane-1-carboxylic acid Chemical class OC(=O)C1CC1(Br)Br ZZQWHIVRLNQEDZ-UHFFFAOYSA-N 0.000 title abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 abstract 3
- HLHNOIAOWQFNGW-UHFFFAOYSA-N 3-bromo-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C=C1Br HLHNOIAOWQFNGW-UHFFFAOYSA-N 0.000 abstract 1
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali-metal salt Chemical class 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 abstract 1
- FAOHDPCUHXSPQY-VHSXEESVSA-N ethyl (1R,3R)-2,2-dichloro-3-phenylcyclopropane-1-carboxylate Chemical compound ClC1([C@H]([C@@H]1C1=CC=CC=C1)C(=O)OCC)Cl FAOHDPCUHXSPQY-VHSXEESVSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- JGCAZFUFORGMFB-UHFFFAOYSA-N methyl 2,2-dichloro-1-methylcyclopropane-1-carboxylate Chemical compound COC(=O)C1(C)CC1(Cl)Cl JGCAZFUFORGMFB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- ULKADLGGTPAKSU-UHFFFAOYSA-M sodium;2,2,2-tribromoacetate Chemical compound [Na+].[O-]C(=O)C(Br)(Br)Br ULKADLGGTPAKSU-UHFFFAOYSA-M 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
2,2-Dichloro- and 2,2-dibromo-cyclopropane carboxylic acids and substitution products thereof are prepared by the action of an alkali-metal salt of trichloro -or tribromo-acetic acid on an alkyl ester of an unsaturated acid of the formula R(R1)C=C(R11)COOH, in which R, R1 and R11 are hydrogen atoms or alkyl or aryl groups, in any permutation, followed by alkaline or acid hydrolysis of the resulting 2,2-dichloro- or 2,2-dibromo-cyclopropane carboxylic ester to yield the free acid. In the examples, (1) methyl methacrylate and sodium trichloracetate yield methyl 1-methyl-2, 2-dichlorocyclopropane carboxylate, which is hydrolysed with hydrochloric acid to yield the free acid; (2) ethyl cinnamate and sodium trichloracetate yield ethyl trans-2, 2-dichloro -3- phenylcyclopropane carboxylate, which is hydrolysed with hydrochloric acid to yield the free acid; the corresponding 2,2-dibromo compound is obtained if sodium tribromoacetate is used instead of sodium trichloracetate. Specification 978,351 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS203060 | 1960-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB978352A true GB978352A (en) | 1964-12-23 |
Family
ID=5356191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1057561A Expired GB978352A (en) | 1960-03-25 | 1961-03-23 | Preparation of 2,2-dichloro-and 2,2-dibromo cyclopropanecarboxylic acids |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH407989A (en) |
| DE (1) | DE1189990B (en) |
| GB (1) | GB978352A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856976A (en) * | 1971-04-23 | 1974-12-24 | Shell Oil Co | Cyclopropane derivative fungicides |
| CN104447293A (en) * | 2014-10-30 | 2015-03-25 | 盐城师范学院 | Method for preparing 1-methyl cyclopropane carboxylic acid |
| CN117603014A (en) * | 2018-11-26 | 2024-02-27 | Fmc公司 | Metadiamide compounds used to control invertebrate pests |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220591A (en) * | 1975-11-26 | 1980-09-02 | Commonwealth Scientific And Industrial Research Organization | Insecticidal esters |
-
1961
- 1961-03-17 CH CH324561A patent/CH407989A/en unknown
- 1961-03-18 DE DEC23682A patent/DE1189990B/en active Pending
- 1961-03-23 GB GB1057561A patent/GB978352A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856976A (en) * | 1971-04-23 | 1974-12-24 | Shell Oil Co | Cyclopropane derivative fungicides |
| CN104447293A (en) * | 2014-10-30 | 2015-03-25 | 盐城师范学院 | Method for preparing 1-methyl cyclopropane carboxylic acid |
| CN104447293B (en) * | 2014-10-30 | 2016-03-23 | 盐城师范学院 | A kind of method for preparing 1-methylcyclopropyl formic acid |
| CN117603014A (en) * | 2018-11-26 | 2024-02-27 | Fmc公司 | Metadiamide compounds used to control invertebrate pests |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1189990B (en) | 1965-04-01 |
| CH407989A (en) | 1966-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1387447A (en) | Carboxylic acids and derivatives | |
| GR34667B (en) | METHOD FOR THE PREPARATION OF ESTERS AND AMIDS OF CARBOXYLIC ACIDS. | |
| GB1299333A (en) | Preparation of carotenoid compounds | |
| GB978352A (en) | Preparation of 2,2-dichloro-and 2,2-dibromo cyclopropanecarboxylic acids | |
| GB1318455A (en) | Production of glycerin and monoesters thereof | |
| GB1298075A (en) | Production of di-neo dicarboxylic acids | |
| GB916772A (en) | Process for the production of a dicarboxylic acid ester | |
| GB1046849A (en) | A new dicarboxylic acid derived from glycyrrhetinic acid | |
| GB1241570A (en) | Process for the preparation of l-and dl-2-guanidino-1,3-thiazoline carboxylic acid-4, and use thereof | |
| SE7908597L (en) | SET TO MAKE KETOIC ACIDS AND ESTERS | |
| GB1318456A (en) | Production of glycerin and diesters thereof | |
| GB1005641A (en) | Dihalocarbene addition products of unsaturated carboxylic acids | |
| GB941393A (en) | Pentafluorosulphur-substituted carboxylic acids | |
| GB902371A (en) | Improvements in additives | |
| GB752876A (en) | Improvements in and relating to bis-aryl-hydrazo compounds | |
| GB1022869A (en) | New derivatives of glycyrrhetinic acid | |
| GB1456487A (en) | Esterification process for preparation of fatty acid esters | |
| GB614772A (en) | The manufacture of esters of pyridyl-3-carbinol | |
| ES364711A1 (en) | Procedure for the preparation of new derivatives of sulfanilamide. (Machine-translation by Google Translate, not legally binding) | |
| GB1292662A (en) | Bicycloheptaneheptanoic acids and esters thereof | |
| GB908177A (en) | Preparation of carboxylic acid fluorides | |
| GB1055927A (en) | 24-nor-5-ß-cholane steroids | |
| GB1019569A (en) | Esters of 1ª‡,2ª‡-methylene-í¸-androstene-3,17ª‰-diol and a process for their manufacture | |
| GB977961A (en) | Monocarboxylic acids containing a pentafluorophenyl nucleus and methods for preparing them | |
| ES355041A2 (en) | A procedure for the preparation of carboxylic acids and their steres, derived from the cyclopropan. (Machine-translation by Google Translate, not legally binding) |