Phthalic acid, 3-Hydroxy

Carboxyphenyl-(2-methyl-3-indoleninjdidene)methanol (303) was said to be formed by the action of phthalic anhydride on 2-methyl-indole magnesium bromide. Skatole magnesium bromide, on the other hand, apparently gave 2-carboxyphenyl-(3-methyl-2-indole-ninylidene)methanol (304) and 3-hydroxy-3-(3-methyl-l-indolyl)-phthalide (305) on treatment with 1 mole of phthalic anhydride. The derivative 305 was easily hydrolyzed in alkali, giving skatole and phthalic acid, and was thus formulated as a 1-skatolyl derivative. ... 

Lead dioxide as oxidizing agent for conversion of 2-hydroxy-3-methyl-benzoic add to 2-hydroxyiso-phthalic acid, 40, 48 Lithium aluminum hydride, in purification of 1,2-dimethoxyethane, 41, 97... 

Hie most representative member of this class of polyesters is the low-molar-mass (M 1000-3000) hydroxy-terminated aliphatic poly(2,2/-oxydiethylene adipate) obtained by esterification between adipic acid and diethylene glycol. This oligomer is used as a macromonomer in the synthesis of polyurethane elastomers and flexible foams by reaction with diisocyanates (see Chapter 5). Hydroxy-terminated poly(f -caprolactonc) and copolyesters of various diols or polyols and diacids, such as o-phthalic acid or hydroxy acids, broaden the range of properties and applications of polyester polyols. 

Figure 12.12 THM GC/MS curves of a Winsor Newton lemon alkyd paint (a) and of an alkyd sample taken from Fontana s work Concetto spaziale (1961) (b). Peak assignments 1, 1,3 dimethoxy 2 propanol 2, 1,2,3 trimethoxy propane 3, 3 methoxy 1,2 propandiol 4, 4 chloro benzenamine 5, 3 methoxy 2,2 bis(methoxymethyl) 1 propanol 6, 3 chloro N methyl benzenamine 7, 3 methoxy 2 methoxymethyl 1 propanol 8, 4 chloro N methyl benzenamine 9, phthalic anhydride 10, 3 chloro 4 methoxy benzenamine 11, suberic acid dimethyl ester 12, dimethyl phthalate 13, azelaic acid dimethyl ester 14, sebacic acid dimethyl ester 15, palmitic acid methyl ester 16, oleic acid methyl ester 17, stearic acid methyl ester 18, 12 hydroxy stearic acid methyl ester 19, 12 methoxy stearic acid methyl ester 20, styrene 21, 2 (2 methoxyethoxy) ethanol 22, 1,1 oxybis(2 methoxy ethane) 23, benzoic acid methyl ester 24, adipic acid dimethyl ester 25, hexadecenoic acid methyl ester 26, dihydroisopimaric acid methyl ester 27, dehydroabietic acid methyl ester 28, 4 epidehydroabietol...

Biological. A proposed microbial degradation mechanism is as follows 4-hydroxy-3-methylbenzyl alcohol to 4-hydroxy-3-methylbenzaldehyde to 3-methyl-4-hydroxybenzoic acid to 4-hydroxyisophthalic acid to protocatechuic acid to p ketoadipic acid (Chapman, 1972). In anaerobic sludge, diethyl phthalate degraded as follows monoethyl phthalate to phthalic acid to protocatechuic acid followed by ring cleavage and mineralization (Shelton et al, 1984). 

BA BuE-PA BE-HET BE-HHPA BE-MA BE-PA BE-SA CA CHX DMA DMBA DY 062 GA HEB HHPA HMTA MA MTHPA NMA benzoic acid monobutylester of phthalic acid monobenzylester of hexachloroendomethylenetetrahydrophthalic acid monobenzylester of hexahydrophthalic acid monobenzylester of maleic acid monobenzylester of phthalic acid monobenzylester of succinic acid citraconic anhydride cyclohexanol N,N-dimethylaniline dimethylbenzylamine high boiling tertiary amine (Ciba Geigy AG) gjptaric anhydride 2-hydroxy-4-(2,3-epoxypropoxy)benzophenone hexahydrophthalic anhydride hexamethylenetetramine maleic anhydride methyltetrahydrophthalic anhydride nadic methyl anhydride (methylbicyclo[2.2.1]heptene-2,3-dicarboxylic anhydride isomers)... 

All three of the isomeric di-hydroxy benzenes are known and their respective constitutions have been established through their relationships to the three xylenes and the three phthalic acids (p. 687). 

The remarkable thing is, that while there are ten possible di-brom or di-hydroxy anthraquinones, the particular one necessary was obtained by Graebe and Liebermann. The positions of the two hydroxyl groups were determined by Baeyer and Caro. When alizarin is heated pyro-catechinol, i-2-di-hydroxy benzene, is obtained. Also when pyro-catechinol is heated with ortho- hXhaXic acid and sulphuric acid alizarin results. This last synthesis is analogous to that of anthraquinone from benzene and o //io-phthalic acid (p. 796). 

This relationship of alizarin to pyro-catechinol proves that the two hydroxyl groups must be ortho to each other, but this condition is possible if the hydroxyls are either 1-2 or 2-3. Baeyer and Caro established the positions as 1-2 as follows. When phenol is heated with ortho-phthalic acid and sulphuric acid two mono-hydroxy anthraquinones are obtained. 

Type II hydrogen abstraction by the keto group from the adjacent aryl methyl group to give the biradical (60) from which both products (61) and (62) are formed. The reaction is solvent dependent. In cyclohexane solvent only the cyclobutanols (61) are formed, but in methanol a mixture of (61) and the new diketone (62) are obtained in a ratio which is dependent upon steric factors. The photochemically induced proton transfer in 3-methyl-6-hydroxy-m-phthalic acid has been reported. ... 

The most important industrial use of pentaerythritol is in a wide variety of paints, coatings, and varnishes, where the cross-linking capability of the four hydroxy groups is critical. Alkyd resins (qv) are produced by reaction of pentaerythritol with organic acids such as phthalic acid or maleic acid and natural oil species. 

Phthalic acid, benzyl 3-hydroxy-1-isopropyl-2,2-dimethylpropyl ester isobutyrate. 

Benzyl 3-isobutyryloxy-1-isopropyl-2,2-dimethylpropyl phthalate EINECS 240-920-1 Phthalic acid, benzyl 3-hydroxy-1-isopropyl-2,2-dimethylpropyl ester isobutyrate. 

Simple alcohols with only one hydroxy function and one asymmetric carbon atom are classical chiral chemicals. While they are often commercially available, they are relatively expensive. Until recently, they were obtained mainly by resolution of the racemates using a reliable but not very convenient technique. Reaction of the racemic alcohol with phthalic acid anhydride gave the monoester of phthalic acid, which was resolved by salt formation with a chiral base, usually brucine, or occasionally also strychnine or cinchonidine. The methyl carbinols from 2-butanol 1 to 2-tridecanol were first obtained by this method1,2 and this was later extended to 3,3-dimethyl-2-butanol3. When crystallization of the diastereomeric salts was performed in the presence of triethylamine, some other methyl carbinols could also be resolved, such as... 

Fig. 4. Hydrogenation of the ring of acid-substituted aromatic compounds using 5% Rh on AhOa powder as catalyst and 100 ml. solvent. 1) 1 g. catalyst, 0.5 ml. benzene, HOAc 2) 1 g. catalyst, 500 mg. benzoic acid HOAc 3) 1 g. catalyst, 500 mg. phthalic acid, HaO 4) 1 g. catalyst, 500 mg. m-hydroxy-benzoic acid, HOAc 5) 1 g. catalyst, 500 mg. phthalic acid, HOAc 6) 1 g. catalyst, 500 mg. salicylic acid, HOAc 7) 1 g. catalyst, 500 mg. p-hydroxy-benzoic acid, HOAc.

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