ES374590A1 - PROCEDURE FOR OBTAINING ACE-TIC ACID DERIVATIVES BIS - (PHENOXISUSTITUIDOS). - Google Patents
PROCEDURE FOR OBTAINING ACE-TIC ACID DERIVATIVES BIS - (PHENOXISUSTITUIDOS).Info
- Publication number
- ES374590A1 ES374590A1 ES374590A ES374590A ES374590A1 ES 374590 A1 ES374590 A1 ES 374590A1 ES 374590 A ES374590 A ES 374590A ES 374590 A ES374590 A ES 374590A ES 374590 A1 ES374590 A1 ES 374590A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- group
- formula
- see formula
- hydrogen
- 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 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 16
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 4
- -1 bis- (substituted phenoxy) acetic acid Chemical class 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 239000000460 chlorine Substances 0.000 abstract 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 229910052740 iodine Inorganic materials 0.000 abstract 3
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 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
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 125000004799 bromophenyl group Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 abstract 1
- 229940031826 phenolate Drugs 0.000 abstract 1
- 239000002904 solvent Substances 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 R represents a hydrogen atom or the residue of a monohydric alcohol capable of forming an ester by reaction with an acid, each of R1 and R2, which may be the same or different, represent 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, represent a hydrogen, chlorine, bromine or iodine atom, with the conditions that i) at least one of R1 and R2 does not mean hydrogen, ii) R1 and R2 can both be chlorine atoms, and R3 and R4 can both be hydrogen atoms, only when R does not represent a hydrogen atom, a residue of a saturated aliphatic alcohol containing 1 to 6 carbon atoms, piperidine, cyanomethyl, di [carbalkoxy) methyl, where "alkoxy" represents an alkoxy group containing 1 to 4 carbon atoms, or a residue A of an alcohol A-OH, where it represents a group of formula - (CHRO) nR' ; (see formula), (finding the connection point either in position 2 or 3); (see formula) (finding the connection point in either position 2, 5 or 4); **(See formula)** (the point of connection being in position 2 or 3); (see formula) (finding the connection point either in position 2 or 3); **(See formula)** (the point of connection being in position 2 or 3); (see formula) (with the connection point being in position 2, 3 or 4); **(See formula)** (the point of connection being in position 2, 3 or 4); 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 either at position 2, 3 or 4); **(See formula)** (the point of connection being in position 2 or 3); **(See formula)** (the point of connection being in position 2 or 3); **(See formula)** (the point of connection being in position 2 or 3); **(See formula)** and when n represents 2, 3 or 4 and Rº represents a hydrogen atom, R'also represents a) an anilino or N-alkyl-anilino radical, the alkyl group of which contains from 1 to 4 carbon atoms, or b) a radical of formula **(See formula)** R ° 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, R6 represents an alkyl group containing from 1 to 4 carbon atoms, a propargyl, phenyl, chloro- or bromo-phenyl group, or a phenyl-alkyl group, the alkyl moiety of which contains from 1 to 4 carbon atoms, represents an atom hydrogen, an alkyl group containing 1 to 4 carbon atoms, a cycloalkyl group containing 5 to 7 ring carbon atoms, a phenyl or phenyl-alkyl group, the alkyl moiety of which contains 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 group, or phenyl-alkyl, the alkyl moiety of which contains 1 to 4 carbon atoms, with the proviso that when it represents a hydrogen atom, R8 represents a phenyl group, iii) R1, R2, R3 and R4, which may be the same or different, may all be selected from the group consisting of a hydrogen, chlorine, bromine or iodine atom, when R does not represent a hydrogen atom or an alcohol residue saturated aliphatic containing 1 to 6 carbon atoms, iv) R1 and R3 which are the same, can be selected from the group consisting of a trifluoromethyl, phenyl, p-chlorophenyl or p-bromophenyl group, and y can both be hydrogen atoms, only when R does not represent a hydrogen atom, the residue of a saturated aliphatic alcohol containing 1 to 6 carbon atoms, or such group of formula, **(See formula)** where n'' represents an integer from 0 to 4, n'''represents 4 or 5, and represents an alkyl radical of 1 to 4 carbon atoms, the point of attachment of the heterocyclic ring being in any of the available positions, and v) R1 and R2 can be selected from the group consisting of a trifluoromethyl or phenyl group or a hydrogen atom, provided that at least one of R1 and R2 does not mean a hydrogen atom, and R3 and R4 can be hydrogen, only when R does not represent a hydrogen atom or the residue of a saturated aliphatic alcohol containing from 1 to 6 carbon atoms, characterized in that a compound is reacted in a solvent that is inert under the reaction conditions of formula II, **(See formula)** with a corresponding compound of formula III, **(See formula)** as phenolate or in the presence of a haloidic acid binding agent, in whose formulas II and III R, R1, R2, R3, R4, X and the conditions are as defined in relation to the formula I indicated above, and Y represents a hydrogen atom or a group of the formula -COOR, where R has the meaning indicated above, with the proviso that when Y represents a group of the formula -COOR, 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 |
|---|---|
| ES374590A1 true ES374590A1 (en) | 1972-04-01 |
Family
ID=25715518
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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) |
| ES374590A Expired ES374590A1 (en) | 1968-10-18 | 1969-12-16 | PROCEDURE FOR OBTAINING ACE-TIC ACID DERIVATIVES BIS - (PHENOXISUSTITUIDOS). |
| ES374591A Expired ES374591A1 (en) | 1968-10-18 | 1969-12-16 | PROCEDURE FOR OBTAINING ACE-TIC ACID DERIVATIVES BIS - (PHENOXISUSTITUIDOS). |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES374591A Expired ES374591A1 (en) | 1968-10-18 | 1969-12-16 | PROCEDURE FOR OBTAINING ACE-TIC ACID DERIVATIVES BIS - (PHENOXISUSTITUIDOS). |
Country Status (2)
| Country | Link |
|---|---|
| CH (4) | CH523218A (en) |
| ES (3) | ES374592A1 (en) |
-
1969
- 1969-10-06 CH CH47372A patent/CH523218A/en not_active IP Right Cessation
- 1969-10-06 CH CH47072A patent/CH523215A/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
- 1969-12-16 ES ES374592A patent/ES374592A1/en not_active Expired
- 1969-12-16 ES ES374590A patent/ES374590A1/en not_active Expired
- 1969-12-16 ES ES374591A patent/ES374591A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH523215A (en) | 1972-05-31 |
| ES374591A1 (en) | 1972-04-01 |
| CH523218A (en) | 1972-05-31 |
| CH523217A (en) | 1972-05-31 |
| CH520094A (en) | 1972-03-15 |
| ES374592A1 (en) | 1972-04-01 |
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