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United States Patent Office Patented June 28, 1932 1,865,096 UNITED STATES PATENT OFFICE SEBASTIAN GASSNER, OF LEVERKUSEN-ON-THE-RHINE, AND BERTHOLD BIENERT, OF COLOGN E-ON ~‘1‘HE-RHINE, GERMANY, ASSIGNORS TO GENERAL ANILIN E WORKS, INCL, OF NEW’ YORK, N. Y., A CORPORATIONHOF DELAWARE MANUFACTURE OF ALKOXYBENZOPHENONE 131- OR TRICARBOXYLIC ACIDS No Drawing; Application filed February 7, 1930, Serial No. 426,764, and. in Germany February 13, 1929. The present invention relates to a process and wherein the benzene nuclei may be sub for preparing. alkoxybenzophenone di- or stituted as mentioned for the starting mate~ tricarboxylic acids andto new products 0b rials, separate in a very pure state and in a : tainable thereby. (in yield between about 75—100% of the theoreti 65 “7e have found that alkoxybenzophenone cal amount. They form colorless crystals di- or tricarboxylic acids can easily be pre soluble in strong sulfuric acid with a yellow pared in a good yield and in an excellent coloration. Obviously instead of the free state of purity by reacting with a water benzophenone monocarboxylic acids also the in soluble permanganate, such as ammonium-, alkalimetal salts of the same may be used, 60 sodium-, potassium—, calcium permanganate addition of an alkali not being necessary in or the like upon a compound of the probable this case. i formula ' The starting materials, that is to say the compounds of the general Formula I may be 15 /0 prepared, for example, by reacting with a 65 substituted or unsubstituted phtha-lic anhy clride upon a cresol or xylenole in the pres ence of aluminium chloride/sodium chloride wherein a means one of the numbers 1 or 2 at 120—150° C. or in the presence of alumi 20 and wherein the benzene nuclei may be fur nium chloride with the addition of suitable 70 ther substituted by monovalent substituents, solvents, such as trichlorobenzene, acethylene such as hydroxy groups, alkoxy groups, tetrachloride or the like at a temperature of halogen atoms or the like. about 100-150° C. or in the presence of boric , The reaction may be performed by intro acid at 80-210o C, and alkylating the reaction 25 ducing the benzophenone monocarboxylic products, for example, by, means of dimethyl~ acid into water, adding an alkali, such as sulfate in the presence of caustic soda lye at soda, potash, caustic soda, ammonia or the about 80—100° C. like until the benzophenone monocarboxylic, The following examples illustrate our in acid has dissolved (a slight excess of the al vention without restricting it thereto, the 30 kali being advantageous in many cases) and parts being by Weight. 80 reacting upon this solution with a water solu ble permanganate, especially sodium per Example 1 manganate at a. temperature between about 10 parts of 4’-methoxy-5'-methyl-benzoyl 50~100° C. The permanganate is advan~ o-benzoic acid of a melting point of 185—l87° 35 tageously applied in an amount surmount C. (obtainable from 4’-hydroxy-5’-methyl ing that being theoretically necessary for benzoyl-o-benzoic acid of a melting point of the oxidation of the methyl groups, esp'ecial- " 229—230° C. by treating same with dimethyl ly in the case that the starting materials sulfate or p-toluenesulfonic acid ether in the have been applied in a rather impure state. presence of caustic soda lye, or by condensing 40 Reaction will be complete within some hours o-cresol methylether with phthali‘c anhy-I in the most cases, after which time the re dride) are dissolved in 10-20 parts of water action mixture is ?ltered and the ?ltrate with‘the calculated or a surplus quantity of acidified. The reaction products which prob soda or caustic soda lye, and the solution is ably correspond to the general formula oxidized for 1-—11/2 hours with 15—18 parts of .45 ‘ (I? O—alky1 potassium permanganate, being introduced 95 /O\ in small portions, at a temperature of 70 ————(COOH)n 100° C. The surplus potassium permanga nate is decomposed by the addition of bisul- - \oooH ?te, the reaction mass is ?ltered from pyro 50 wherein 12 means one of the numbers 1 or 2 lusite, the acid formed precipitated from the" 100 1,865,096 ?ltrate with hydrochloric acid while boiling, acid formed precipitated from the ?ltrate and the crystallized acid is ?ltered off after with hydrochloric acid while boiling. The cooling. The 4’ - methoxy - benzophenone - colorless 2’ - methoXy-5’ - chloro - benzophe - 2.5’-dicarboxylic acid thus obtained melts at none-2.4’-dicarboxylic acid thus obtained 234-2350 C. melts at 202-204:0 C. 70 E wample 2 0on3 oorra (‘10113 (‘mm | 00 co / \ on; —o0,11 -—-> 75 10 U00 0 /o o\ \ \ \COzH \om \OO2H c0211 COzH I 00211 I 10 parts of 2’-methoXy-4J-methyl~benzoyl om com o-benzoic acid of a melting point of 115° C. 10 parts of 2’-1nethoXy-3’.5’-dimethyl-ben (obtainable from 2’-hydroXy-LF-methyl-bem zoyl-o-benzoic acid of a melting point of 123 80 15 zoyl-o-benzoic acid of a melting point of 211— 126° C. (obtainable from 2’-hydroXy-3’.5’~ 213° C. by treating same with dimethyl sul dimethyl-benzoyl-osbenzoic acid of a melting fate-or p-toluenesulfonic acid methylether in point of 173-174" C. bytreating same with the presence of caustic soda lye) are dissolved dimethyl sulfate or p-toluene sulfonic acid in 10~20 parts of water and oxidized as de methyl ether in the presence of caustic soda scribed in Example 1. The 2’-methoXy-ben lye) are dissolved in 10—20 parts of water and zophenone - 2.ét’-dicarboxylic acid thus the solution is oxidized for 11/2—2 hours with formed melts at 249—250° C. 30410 parts of potassium permanganate, at a temperature of 70—100° C. After decompo _ E wample 3 sition of the surplus potassium permanganate, 00 ' 00113 00113 the reaction mass is ?ltered from pyrolusite and strongly acidified with hydrochloric acid /oo I /oo\ I while boiling. The 2’-methoXy-benzophen one-2.3’.5’-tricarboXylic acid crystallizing out after cooling melts at 140—142° C. r: In 30 Osman O\CO2H CH3 02H E mampl e 6 10 parts of 2’~methoxy~5’-methyl-benzoyl-o 00m 00m benzoic acid of a melting point of 156—158° C. (obtainable by treating 2’-hydroXy-5’~ /3\\/G°\/)2\4 2 1 3 q/CO\ methyl-benzoyl-o-benzoic acid of a melting 100 point of 196—197° C. with dimethyl sulfate 5 1 t L6 41 a L/ orp-toluenesulfonic acid methylether in the 6 A0 02H 5// c0211 presence of caustic soda lye or by condensing 01 cm c1 0021i p-cresolmethylether with phthalic anhy—' 10 parts of 2’-methoXy-5'methyl-6-chloro dride) are dissolved in 10-20 parts of Water benzoyl-2-benzoic acid of a melting point of : 40 and oxidized as described in Example 1. 186-1870 C. (obtainable from 2’-hydroXy-5’ The 2’-methoxy—benzophenone-2.5’~dicarbo methyl-6-chloro-benzoyl-2-benzoic acid of a Xylic acid thus obtained melts at 238—289° C. melting point of 257—258° C. by treating same E wample 4 with dimethylsulfate in the presence of caus 45 00m 00m tic soda lye) are dissolved in 30-40 parts of i water with 3, 41-3, 6 parts of soda and the solu tion is oxidized {or 3—4 hours with 15—16 parts /oo 1 __, 0/0 o\ I of potassium permanganate at '80—90° C. com \OHa \coin COzH The surplus potassium permanganate is de 50 1 c1 I composed by the addition of bisul?te, the re 10 parts of 2’-methoXy-4’-methyl-5’~chloro action mass is ?ltered from pyrolusite and benzoyl-o-benzoic acid of a melting point of the ?ltrate is strongly acidi?ed with hydro 172—173° C. (obtainable from 2’-hydroXy-4:’ chloric acid while boiling. The precipitating methyl-5’-chlorobonzoyl-o-benzoic acid of a 2’-methoXy-6-cl1lorobenzopl1enone-2,5’-dicar melting point of 205—207° C. by treating same boxylic acid is ?ltered off after cooling. It with dimethylsulfate or p~toluenesulfonic melts at 294.—296° C. acid methylether in the presence of caustic Example '7 soda lye or by condensing p-chloro-m- cresol )ofm OCHs| methylether with phthalic anhydride) are /\ co CO 1 dissolved in 10-20 parts of water and oxidized / 3 / \/ 2 / with 14—20 parts of potassium permanganate i4 2 1 3 ——>V for 11/2—2 hours at 70-100" C. After decom 5 1 s 5 4_OH3 \ COzH position of the surplus potassium perman \i (10211 1/ I 00211 ganate by the addition of bisul?te, the reac I I C1 C1 65 tion mass is ?ltered from pyrolusite and the 10 Parts’ of 2'-me?10Xy-4’-methy1-6.5’-di 1,865,096 3 chlorobenzoyl-2-benzoic acid of a melting 4. The products of the probable general point of 198-200° C. (obtainable from 2'~ formula hydroxy-éL'-methyl - 6,5'- dichloro-benzo 1-2 0-a1kyl benzoic acid of a melting point of 232° . by 3 treating same with dimethylsulfate in the presence of caustic soda lye) are dissolved in Of --—(COOH)-. 50-60 parts of water with 3, 2-3, 4 parts of COOH soda and the solution is oxidized for 6-8 hours wherein it means one of the numbers 1 or 2 and with 14-15 parts of potassium permanganate, wherein the benzene nuclei may be further 10 at a temperature of 80—90° C.
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