GB605737A - Improvements in or relating to the production of esters of hydroxy-alkoxy benzoic acids - Google Patents
Improvements in or relating to the production of esters of hydroxy-alkoxy benzoic acidsInfo
- Publication number
- GB605737A GB605737A GB3431245A GB3431245A GB605737A GB 605737 A GB605737 A GB 605737A GB 3431245 A GB3431245 A GB 3431245A GB 3431245 A GB3431245 A GB 3431245A GB 605737 A GB605737 A GB 605737A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butyl
- acid
- dihydroxypropoxy
- ester
- prepared
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Esters of hydroxyalkoxy-benzoic acids of the general formula <FORM:0605737/IV(b)/1> wherein the -OCH2CHOHCH2OH group is in the ortho-, meta- or para-position to the COOR group, X represents hydrogen, an alkyl group including unsaturated alkyl, a substituted hydroxyl group or a nitro group and R represents an alkyl or an hydroxyalkyl group, are prepared either by esterifying a hydroxybenzoic acid to form an ester of the acid and thereafter reacting the ester with an a -mono-halogenohydrin, or reacting the hydroxybenzoic acid with an a -monohalogenohydrin to form the b : g -dihydroxypropoxybenzoic acid and thereafter converting the b : g -dihydroxypropoxybenzoic acid to the required ester. Normal methods for the formation of esters from acids may be employed, e.g. the hydroxybenzoic or b : g -dihydroxypropoxybenzoic acid may be treated with an alcohol and acid or with a diazohydrocarbon, or the substituted benzoic acid may be converted into the corresponding acid halide which is then reacted with an alcohol or metal alcoholate, or an ester of the substituted benzoic acid may be converted into another ester by treatment with the metal alcoholate corresponding to the alcohol of the ester required, or an ester of hydroxybenzoic acid may be reacted with an a -monohalogenohydrin to form the ester of the b : g -dihydroxypropoxybenzoic acid which ester is hydrolysed to form the free acid which may then be esterified. In examples: (1) to (12) and (19), the preparation of the ethyl, n-propyl and n-butyl esters of p-hydroxybenzoic and p-(b : g -dihydroxypropoxy) benzoic acids and the methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, n-amyl, iso-amyl and hexyl esters of m-hydroxybenzoic and m-(b : g -dihydroxypropoxy) benzoic acids is described; (13) and (14), the ethyl and n-butyl esters of o-(b : g -dihydroxypropoxy) benzoic acid are prepared; (15) b - hydroxyethyl - o - (b : g - dihydroxypropoxy)-benzoate is prepared; (16), (17), (18), (20) and (21), butyl esters of nitro-(b : g -dihydroxypropoxy) benzoic acids are prepared, including n - butyl - 3 - nitro - 4 - (b : g - dihydroxy - propoxy) benzoate and n - butyl - 4 - nitro - 3 - (b : g - dihydroxypropoxy) - benzoate; (22) and (23) methyl - m - (b : g - dihydroxypropoxy) ben - zoate and buty-3-allyl-4-(b : g -dihydroxypropoxy) benzoate are prepared. n-Butyl-3-nitro-4-hydroxybenzoate and n-butyl-4-nitro-3-hydroxybenzoate are prepared by nitrating n-butyl-p-hydroxybenzoate and n-butyl-m-hydroxybenzoate respectively. n - Butyl - 3 - amino - 4 - (b : g - dihydroxypropoxy) benzoate and n-butyl-4-amino-3-(b : g -dihydroxypropoxy) benzoate are prepared by reducing the corresponding nitro substituted compounds with hydrogen and Raney nickel. n - Butyl - 3 - diethylamino - 4 - (b : g - dihydroxy - propoxy) benzoate is prepared by refluxing the corresponding amino substituted compound with ethyl iodide.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3431245A GB605737A (en) | 1945-12-18 | 1945-12-18 | Improvements in or relating to the production of esters of hydroxy-alkoxy benzoic acids |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3431245A GB605737A (en) | 1945-12-18 | 1945-12-18 | Improvements in or relating to the production of esters of hydroxy-alkoxy benzoic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
GB605737A true GB605737A (en) | 1948-07-29 |
Family
ID=10364066
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3431245A Expired GB605737A (en) | 1945-12-18 | 1945-12-18 | Improvements in or relating to the production of esters of hydroxy-alkoxy benzoic acids |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB605737A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2963474A (en) * | 1958-07-23 | 1960-12-06 | Mallinckrodt Chemical Works | Organic compounds |
US3198827A (en) * | 1960-05-09 | 1965-08-03 | Boehringer Sohn Ingelheim | Hydroxy-benzoic acid ethers and salts thereof |
-
1945
- 1945-12-18 GB GB3431245A patent/GB605737A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2963474A (en) * | 1958-07-23 | 1960-12-06 | Mallinckrodt Chemical Works | Organic compounds |
US3198827A (en) * | 1960-05-09 | 1965-08-03 | Boehringer Sohn Ingelheim | Hydroxy-benzoic acid ethers and salts thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB1456359A (en) | Biphenyl carboxylic esters | |
GB605737A (en) | Improvements in or relating to the production of esters of hydroxy-alkoxy benzoic acids | |
GB690816A (en) | Improvements in or relating to the manufacture of substituted phenoxy acetic acids | |
ES338638A1 (en) | New substituted phenylacetic esters, their production and compositions containing them | |
GB1174535A (en) | Substituted Phenylacetic acids and process of preparation thereof | |
GB1417174A (en) | 1-2-delta2-imidazolinyl-2,2-diarylcoclopropanes | |
ES379619A1 (en) | A process for the manufacture of amino acids and derivatives thereof | |
GB993754A (en) | Improvements in or relating to novel thyromimetic compounds | |
GB1046849A (en) | A new dicarboxylic acid derived from glycyrrhetinic acid | |
GB708065A (en) | Improvements in the production of photographic images | |
ES395599A1 (en) | Orally administered contrast agents for cholecystography | |
GB667199A (en) | Process for stabilizing photographic emulsions | |
GB1144829A (en) | Tricyclic derivatives of acetamide | |
ES446239A1 (en) | 8-azaprostaglandins and process for the preparation thereof | |
ES342910A1 (en) | Procedure for the preparation of hydroxyiacides. (Machine-translation by Google Translate, not legally binding) | |
GB1128554A (en) | Processes for the preparation of aliphatic acid esters | |
GB1389984A (en) | Sulphuric and phosphoric acid esters of substituted carvacrols | |
GB1107036A (en) | Esters of dibenzocycloheptenyl-carboxylic acids | |
GB661185A (en) | Improvements in or relating to the production of alkoxyalkyl esters of iodobenzoic acids | |
GB767878A (en) | Aminoacid esters | |
GB820503A (en) | Improvements in or relating to the production of n-substituted 2-hydroxymethyl pyrrolidines | |
GB700344A (en) | Improvements in or relating to the manufacture of 21-iodo-pregnene-(5)-ol-(3)-one-(20) | |
GB937378A (en) | Production of phenylethylbenzoic acid compounds | |
GB682823A (en) | Manufacture of 3:3-carbalkoxy-methylene-bis-(4-hydroxy-coumarins) | |
ES363015A1 (en) | Procedure for preparing new amida compounds. (Machine-translation by Google Translate, not legally binding) |