Oxidative breakdown of tetrachloro-o-benzoquinone with peroxyphthalic acid. Study of the oxidation products was written by Karrer, P.;Testa, E.. And the article was included in Helvetica Chimica Acta in 1949.Quality Control of Ethyl methyl adipate The following contents are mentioned in the article:
Tetrachloro-o-benzoquinone and o-HO2CC6H4CO3H give 30.5% tetrachloromuconic acid (I), m. 156.7掳 (di-Me ester, b11 135掳), and 3.5% 伪,尾,未-trichloro-纬-hydroxymuconic acid 纬-lactone (II), m. 182掳, gives a violet solution with NaHCO3 (Me ester (III), from CH2N2, m. 107掳). The yield of II increases in prolonged reactions. Hydrolysis of both I and II gives a mixture of 伪,纬-dihydroxy-尾,未-dichloromuconic acid 纬-lactone (IV), m. 225掳 (decomposition), and 2,3,5-trichloro-4-oxo-2-pentenoic acid (V), m. 107掳 (Me ester, m. 86-7掳). The intermediate in the formation of V is probably 伪,尾,未-trichloro-纬-hydroxymuconic acid, whose keto form loses CO2. Catalytic reduction of V gives EtCO2H and BuCO2H. V and Ca(OCl)2 form (:CClCO2H)2 and CHCl3. IV does not react with HIO4 or AgNO3. With CH2N2 it gives Me 伪-methoxy-尾,未-dichloro-纬-hydroxymuconate lactone (VI), m. 99.5-100掳. III in hot H2O gives Me 伪,纬-dihydroxy-尾,未-dichloromuconate 纬-lactone (VII), m. 166.5-7掳. With CH2N2 VII gives VI. Refluxing VI with H2O gives a compound, m. 167-8掳, which is a Me 伪-methoxydihydroxychloromuconate 纬-lactone, but the location of the free OH and the Cl groups is not determined The mother liquors contain some Me 伪-methoxy-尾,未-dichloro-纬-hydroxymuconate (VIII), m. 100-1掳, but VIII is better obtained from VI with NaOH in MeOH. Catalytic reduction of VIII with Pt in EtOH gives Et Me adipate, b11 115-20掳, and in H2O it gives adipic acid. Reduction with Zn and EtOH-AcOH gives an oil which is probably Me 伪-methoxy-纬-hydroxy-伪,未-dihydromuconate. With CH2N2 this gives a compound, b11 125-30掳, probably the di-Me ester. This study involved multiple reactions and reactants, such as Ethyl methyl adipate (cas: 18891-13-9Quality Control of Ethyl methyl adipate).
Ethyl methyl adipate (cas: 18891-13-9) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Quality Control of Ethyl methyl adipate
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics