ES374591A1 - PROCEDURE FOR OBTAINING ACE-TIC ACID DERIVATIVES BIS - (PHENOXISUSTITUIDOS). - Google Patents
PROCEDURE FOR OBTAINING ACE-TIC ACID DERIVATIVES BIS - (PHENOXISUSTITUIDOS).Info
- Publication number
- ES374591A1 ES374591A1 ES374591A ES374591A ES374591A1 ES 374591 A1 ES374591 A1 ES 374591A1 ES 374591 A ES374591 A ES 374591A ES 374591 A ES374591 A ES 374591A ES 374591 A1 ES374591 A1 ES 374591A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- see formula
- carbon atoms
- finding
- phenyl
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 150000001242 acetic acid derivatives Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 3
- -1 bis- (substituted phenoxy) acetic acid Chemical class 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 229910052740 iodine Inorganic materials 0.000 abstract 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 abstract 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004799 bromophenyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
-
- 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
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—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)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Process for obtaining bis- (substituted phenoxy) acetic acid derivatives of formula I, **(See formula)** wherein each of R1 and R2, which may be the same or different, represents a hydrogen, chlorine, bromine or iodine atom, or a phenyl, p-chlorophenyl, p-iodophenyl, p-bromophenyl or trifluoromethyl group, each of R3 and R4, which may be the same or different, represents a hydrogen, chlorine, bromine or iodine atom, A represents a group of formula - (CHRO) nR'; (see formula) (finding the connection point either in position 2 or 3); (see formula) (with the connection point being in position 2, 3 or 4); (see formula) (finding the connection point either in position 2 or 3); (see formula) (finding the connection point either in position 2 or 3); (see formula) (finding the connection point either in position 2 or 3); (see formula) (finding the connection point either in position 2, 3 or 4; **(See formula)** (the point of connection being in position 2, 3 or 4); **(See formula)** or a 2-dimethylamino-2-methyl-propyl group, n represents an integer from 1 to 4 inclusive, R'represents a group of formula **(See formula)** (the point of connection being in position 2 or 3); (see formula) (finding the link point to either position 2, 3 or 4); (see formula) (finding the connection point either in position 2 or 3); (see formula) (finding the connection point either in position 2 or 3); (see formula) (finding the connection point either in position 2 or 3); **(See formula)** and when n represents 2, 3 or 4, and R0 represents a hydrogen atom, R'also represents a) an aniline or N-alkyl aniline radical, the alkyl group of which contains from 1 to 4 carbon atoms, or b) a radical of formula **(See formula)** R0 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, n'represents 2, 3 or 4 R5 represents a hydrogen, chlorine or bromine atom, or an alkyl group containing from 1 to 4 carbon atoms, Rx2 represents a β- (p-chlorophenoxy) ethyl group, R6 represents an alkyl group containing 1 to 4 carbon atoms, a propargyl, phenyl, chloro- or bromo-phenyl group, or a phenyl-alkyl group, the alkyl moiety of which contains 1 to 4 carbon atoms, R7 represents a hydrogen atom, an alkyl group containing from 1 to 4 carbon atoms, a cycloalkyl group containing from 5 to 7 ring carbon atoms, a phenyl or phenyl-alkyl group, whose alkyl moiety contains from 1 to 4 carbon atoms, or a 1-naphthyl or 2-naphthyl group, R8 represents an alkyl group containing from 1 to 4 carbon atoms, a cycloalkyl group containing from 5 to 7 ring carbon atoms, a phenyl or phenyl-alkyl group, the alkyl moiety of which contains from 1 to 4 carbon atoms, with the proviso that when R7 represents a hydrogen atom, R8 represents a phenyl group, with the conditions that i) at least one of R1 and R2 does not mean hydrogen, and ii) R1 and R2 cannot both be chlorine atoms when R3 and R4 are both hydrogen atoms, characterized in that a corresponding compound of formula **(See formula)** where R1, R2, R3 and R4 are as defined above, Z represents a hydrogen atom or a group of the formula -COORx, and R represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, with an alcohol of formula A-OH, where A has the meaning indicated above, with the proviso that when Z represents a group of formula -COORx, the reaction is carried out at a temperature that is sufficient to cause partial decarboxylation. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76888168A | 1968-10-18 | 1968-10-18 | |
| CH1498369A CH523862A (en) | 1968-10-18 | 1969-10-06 | Process for the production of new bis-phenoxyacetic acids and their esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES374591A1 true ES374591A1 (en) | 1972-04-01 |
Family
ID=25715518
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES374590A Expired ES374590A1 (en) | 1968-10-18 | 1969-12-16 | PROCEDURE FOR OBTAINING ACE-TIC ACID DERIVATIVES BIS - (PHENOXISUSTITUIDOS). |
| ES374592A Expired ES374592A1 (en) | 1968-10-18 | 1969-12-16 | Procedure for the obtaining of derivatives of the acetic acid bis - (fenoxisustituids). (Machine-translation by Google Translate, not legally binding) |
| ES374591A Expired ES374591A1 (en) | 1968-10-18 | 1969-12-16 | PROCEDURE FOR OBTAINING ACE-TIC ACID DERIVATIVES BIS - (PHENOXISUSTITUIDOS). |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES374590A Expired ES374590A1 (en) | 1968-10-18 | 1969-12-16 | PROCEDURE FOR OBTAINING ACE-TIC ACID DERIVATIVES BIS - (PHENOXISUSTITUIDOS). |
| ES374592A Expired ES374592A1 (en) | 1968-10-18 | 1969-12-16 | Procedure for the obtaining of derivatives of the acetic acid bis - (fenoxisustituids). (Machine-translation by Google Translate, not legally binding) |
Country Status (2)
| Country | Link |
|---|---|
| CH (4) | CH523218A (en) |
| ES (3) | ES374590A1 (en) |
-
1969
- 1969-10-06 CH CH47372A patent/CH523218A/en not_active IP Right Cessation
- 1969-10-06 CH CH47172A patent/CH523217A/en not_active IP Right Cessation
- 1969-10-06 CH CH47272A patent/CH520094A/en not_active IP Right Cessation
- 1969-10-06 CH CH47072A patent/CH523215A/en not_active IP Right Cessation
- 1969-12-16 ES ES374590A patent/ES374590A1/en not_active Expired
- 1969-12-16 ES ES374592A patent/ES374592A1/en not_active Expired
- 1969-12-16 ES ES374591A patent/ES374591A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH523217A (en) | 1972-05-31 |
| ES374590A1 (en) | 1972-04-01 |
| CH523215A (en) | 1972-05-31 |
| ES374592A1 (en) | 1972-04-01 |
| CH523218A (en) | 1972-05-31 |
| CH520094A (en) | 1972-03-15 |
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