Hill, Carl M.’s team published research in Journal of the American Chemical Society in 75 | CAS: 1798-04-5

Journal of the American Chemical Society published new progress about 1798-04-5. 1798-04-5 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(4-(tert-Butyl)phenoxy)acetic acid, and the molecular formula is C12H16O3, Product Details of C12H16O3.

Hill, Carl M. published the artcileThe synthesis, properties, and catalytic hydrogenation of several aryloxy substituted ketene monomers and dimers, Product Details of C12H16O3, the publication is Journal of the American Chemical Society (1953), 1084-6, database is CAplus.

p-Me3CC6H4ONa treated with EtCHBrCO2Et in MeOH gave p-Me3CC6H4OCHEtCO2Et which was hydrolyzed to the corresponding acid (I), 63%, m. 87-8.5¡ã (from petr. ether-C6H6) (all m.ps. reported are corrected). Similarly were obtained: p-Me3CC6H4CHBuCO2H, 69%, m. 89-90¡ã, and p-Me3CC6H4CHAmCO2H, 63%, m. 72-3¡ã. The ¦Á-aryloxy acids were converted with SOCl2 to the corresponding acyl chlorides, p-Me3CC6H4OCHRCOCl (II) (R, b.p./mm., % yield, n20D, and d20 given): H (III), 130-2¡ã/5, 90, 1.5162, 1.1128, from p-tert-BuC6H4OCH2CO2H, m. 88-9¡ã; Me (IV), 143-5¡ã/26, 60, 1.5092, 1.0775, from p-Me3CC6H4OCHMeCO2H, m. 86-7¡ã; Et, 131-2¡ã/3, 94, 1.5055, 1.0651; Bu, 143-4¡ã/3, 95, 1.5018, 1.0641; and Am, 149-50¡ã/6, 97, 1.5003, 0.9984. To 0.5 g. II in 100 cc. dry Et2O was added dry NH3 and the crude precipitate filtered off and recrystallized from MeOH to give the amides p-Me3CC6H4OCHRCONH2 (R, m.p., and % yield given): H, 131-2¡ã, 86; Me, 116-17¡ã, 91; Et, 97-9¡ã, 87; Bu, 145-6¡ã, 71; and Am, 86-7¡ã, 76. III in 20 cc. dry C6H6 warmed with an equivalent amount PhNH2 on the water bath gave p-Me3CC6H4OCH2CONHPh, m. 91-2¡ã. Similarly was prepared p-Me3CC6H4OCHMeCONHPh, m. 83-4¡ã. The dehydrochlorination of III as previously described (cf. C.A. 45, 10128i) gave 37% p-tert-butylphenoxyketene dimer (V), m. 85-6¡ã, b5 180-3¡ã. IV gave similarly 55% p-tert-butylphenoxymethylketene dimer (VI), m. 78-9¡ã, b6 147-50¡ã. By the same procedure were prepared the following p-tert-butylphenoxyalkylketene monomers (alkyl, b.p./mm., % yield, n20D, and d20 given): Et (VII), 175-6¡ã/12, 66, 1.5178, 1.0132; Bu (VIII), 169-71¡ã/10, 54, 1.5044, 1.0157; and Am (IX), 132-3¡ã/5, 73, 1.5056, 0.9771. Weighed samples of the ketenes (5-15 g.) in 25 cc. petr. ether were hydrogenated 4-6 hrs. over 2-4 g. Raney Ni at 1500-3500 lb./sq. in. pressure, the mixture filtered, the solvent distilled off, the residue distilled, and the glycol fraction washed with small portions 15% aqueous Na2CO3 and H2O, dried with MgSO4, and redistilled, giving 2 fractions, p-Me3CC6H4OH, m. 94-5¡ã (from petr. ether-C6H6), and glycols corresponding to the ketene dimer. In the case of V, the p-Me3C6H4 was not split off and the only product was 2,4-bis(p-tert-butylphenoxy)-1,3-butanediol dimer, m. 88-9¡ã ; bis(3,5-dinitrobenzoate), m. 140-1¡ã. VI gave by hydrogenation 50% CHMe.CH(OH).CHMe.CHOH, b20 83-4¡ã n20D 1.5328, d20 1.0570; bis(3,5-dinitrobenzoate), 40%, m. 126-7¡ã. The other ketenes were converted similarly to the corresponding CHR.CH(OH).CHR.CHOH (X) [R, % yield, b.p./mm., n20D, d20, and, in parentheses, the % yield and m.p. of the bis(3,5-dinitrobenzoate), given]: Et, 65, 75-7¡ã/10, 1.4458, 0.9165 (37, 165-6¡ã); Bu, 40, 125-6¡ã/3, 1.4343, 0.9108 (35, 162-3¡ã); and Am, 35, 125-7¡ã/5, 1.4388, 0.8957 (50, 163-4¡ã). The 2 isomeric forms of the previously prepared (2,4-Cl2C6H3OCR:C:O)2 (XI), where R is Et, Pr, and Bu, gave by the same procedure the following pairs of isomeric X [R, % yield, b.p./mm., n20D (except where otherwise stated), d20 values and in parentheses, the % yield and m.p. of the bis(p-nitrobenzoate) given]: Et, 55, 60-3¡ã/3, n21D 1.5228, 1.0018 (48, 118-19¡ã), and 40% 2,4-Cl2C6H3OH (XII), m. 42-3¡ã (3,5-dinitrobenzoate, m. 142-3¡ã), from liquid XI with R = Et; Et, 20, 59-61¡ã/3, 1.5362, 1.0784, MRD 41.64 (54, 85-6¡ã), and 35% XII from solid XI with R = Et; Pr, 20, m. 21-3¡ã, 63-5¡ã/3, n25D 1.5362, 1.0757 (56, 88-90¡ã), and 65% XII from liquid XI with R = Pr; Pr, 67, 102-4¡ã/3, 1.5261, 1.0612, MRD 49.76 (68, 114-15¡ã), and 28% XII from solid XI with R = Pr; Bu, 27, 62¡ã/4, 1.5183, 1.0688, MRD) 56.73 (45, 115-16¡ã), and 45% XII from liquid XI with R = Bu; and Bu, 56, 65-8¡ã/2, 1.5299, 1.0378, MRD 59.53 (61, 119-20¡ã), and 38% XII from solid XI with R = Bu.

Journal of the American Chemical Society published new progress about 1798-04-5. 1798-04-5 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(4-(tert-Butyl)phenoxy)acetic acid, and the molecular formula is C12H16O3, Product Details of C12H16O3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia