GB966479A - New substituted salicylic acid derivatives - Google Patents

New substituted salicylic acid derivatives

Info

Publication number
GB966479A
GB966479A GB830463A GB830463A GB966479A GB 966479 A GB966479 A GB 966479A GB 830463 A GB830463 A GB 830463A GB 830463 A GB830463 A GB 830463A GB 966479 A GB966479 A GB 966479A
Authority
GB
United Kingdom
Prior art keywords
benzyl
methyl
compound
formula
saligenin
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
Application number
GB830463A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roche Diagnostics GmbH
Original Assignee
Boehringer Mannheim GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DEB66450A external-priority patent/DE1198831B/en
Priority claimed from DEB69969A external-priority patent/DE1216293B/en
Application filed by Boehringer Mannheim GmbH filed Critical Boehringer Mannheim GmbH
Publication of GB966479A publication Critical patent/GB966479A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
    • C07C47/57—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • 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
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/19—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups having unsaturation outside the aromatic ring

Abstract

The invention comprises compounds of general formula: <FORM:0966479/C1/1> wherein X and Y represent hydrogen or halogen atoms or hydroxyl or C1- 3 alkyl or alkoxy radicals, and A is a straight or branched chain saturated or unsaturated aliphatic hydrocarbon radical containing 2 to 4 carbon atoms; and their preparation by (1) treating a compound of formula: <FORM:0966479/C1/2> or an alkali metal salt thereof, with carbon dioxide, (2) treating a compound of formula: <FORM:0966479/C1/3> with an oxidising agent, (3) treating a compound of formula: <FORM:0966479/C1/4> with a hydrohalic acid, (4) in the preceding processes where the p-position to the phenolic hydroxy group is first blocked with a halogen atom this is split off at the end of the reaction by catalytic hydrogenation, and (5) where A in a compound I is unsaturated, forming the corresponding saturated compound by catalytic hydrogenation. Sodium salts of certain products are mentioned. Starting materials obtained are 3-(a -methyl-benzyl)-5-chloro-saligenin by treatment of 2-(a -methyl-benzyl)-4-chlorophenol with aqueous alkaline formaldehyde; hydrogenation yields 3-(a -methyl-benzyl)-saligenin which can also be obtained by lithium aluminium hydride of 3-(a -methyl-benzyl)-salicylic acid; treatment with methyl iodide yields 2-methoxy-3-(a -methyl-benzyl)-benzyl alcohol, the corresponding benzoic acid being obtained by potassium permanganate oxidation. 3-(a -Methyl-benzyl)-5-chloro-salicyl aldehyde is obtained from the corresponding saligenin using m-nitrobenzene-sulphonic acid sodium salt; 3-(a -methyl-benzyl)-salicyl aldehyde is similarly obtained.
GB830463A 1962-03-21 1963-03-01 New substituted salicylic acid derivatives Expired GB966479A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEB66450A DE1198831B (en) 1962-03-21 1962-03-21 Process for the preparation of 3-aralkylsalicylic acids
DEB69969A DE1216293B (en) 1962-12-13 1962-12-13 Process for the preparation of 3-phenylalkenyl-salicylic acids

Publications (1)

Publication Number Publication Date
GB966479A true GB966479A (en) 1964-08-12

Family

ID=25966191

Family Applications (1)

Application Number Title Priority Date Filing Date
GB830463A Expired GB966479A (en) 1962-03-21 1963-03-01 New substituted salicylic acid derivatives

Country Status (7)

Country Link
AT (1) AT243785B (en)
CH (2) CH443350A (en)
DK (2) DK109782C (en)
FI (2) FI40720B (en)
GB (1) GB966479A (en)
LU (1) LU43384A1 (en)
SE (1) SE312142B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4687869A (en) * 1984-10-22 1987-08-18 Ciba-Geigy Corporation Metal salicylates, process for their preparation and use thereof as color developers in pressure-sensitive or heat-sensitive recording materials
AU2003300358A1 (en) * 2002-12-20 2004-07-22 Migenix Corp. Ligands of adenine nucleotide translocase (ant) and compositions and methods related thereto

Also Published As

Publication number Publication date
DK109147C (en) 1968-03-25
CH479526A (en) 1969-10-15
DK109782C (en) 1968-07-01
FI42093C (en) 1970-05-11
LU43384A1 (en) 1963-05-20
SE312142B (en) 1969-07-07
FI40720B (en) 1969-01-31
AT243785B (en) 1965-11-25
FI42093B (en) 1970-02-02
CH443350A (en) 1967-09-15

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