Quillet, Jean P. published the artcileDismutation of 3,4-dihydronaphthalenic compounds. II., Category: catalysis-chemistry, the publication is Bulletin de la Societe Chimique de France (1967), 255-60, database is CAplus.
cf. CA 64: 14122c. Ketones of the type I were treated with MeMgI to give II. The dismutation of II (R = R1 = R2 = H) gave a mixture containing 1-methyl-1,2,3,4-tetrahydronaphthalene (III) and 1-MeC10H7 (IV). Thus, a mixture of 93 g. PhCH2CH2CH(CO2Et)2 and 800 ml. 5% NaOH was refluxed 3 hrs. to give 90% 4-phenylbutyric acid (V), b15 170-1¡ã. Also prepared were PhCHR2CHR1CHRCO2H (R, R1, R2, b.p./mm., m.p., and % yield given): Me, H, H, -, -, -; H, H, Ph, 185-9¡ã/1, 103-6¡ã, 70; H, Ph, H, 188-9¡ã/0.3, 92-3¡ã, 70; Ph, H, H, -, 70-1¡ã, 70. V (1 mole) was treated with 150 g. SOCl2 to give 4-phenylbutyryl chloride (VI). Similarly prepared were PhCHR2CHR1CHRCOCl (R, R1, and R2 given): Me, H, H; H, H, Ph; H, Ph, H; Ph, H, H. VI (70 g.) was treated with 51 g. AlCl3 in C6H6 and the mixture hydrolyzed with HCl to give 70% 1-tetralone (VII), b12 129-30¡ã. Similarly prepared were I (R, R1, R2, b.p./mm., m.p., and % yield given): H, Me, H, 133-4¡ã/13, -, 74 (semicarbazone m. 189¡ã); Me, H, H, -, -, -; H, H, Ph, 135-40¡ã/0.1, 76¡ã, 81; H, Ph, H, 162-5¡ã/0.1, 64¡ã, 81; Ph, H, H, 170¡ã/0.3, 76¡ã, 79. A solution of 22 g. VII in ether was treated with a solution containing MeMgI (prepared from 23.5 g. MeI and 3.6 g. Mg) to give 57% 1-methyl-1-tetralol, m. 86¡ã, which was dehydrated to give 1-methyl-3,4-dihydronaphthalene (VIII). Similarly prepared were II (R, R1, R2, b.p./mm., n25D, and % yield given): H, Me, H, 116¡ã/18, 1.559, 58; Me, H, H, -, -, -; H, H, Ph, 130-2¡ã/1, -, 80; H, Ph, H, 132-5¡ã/2.5, 1.611, 60; Ph, H, H, -, -, 72 (m. 76¡ã). VII (1 g.) was added dropwise to 7 ml. H2SO4 to give a mixture containing 3% VII, 54% III, and 43% IV. A mixture of 1 g. VIII in 10 ml. HBr azeotrope was refluxed 1 hr. to give a mixture of 64% VIII, 19% III, and 17% IV. A mixture of 1 g. VIII and 10 ml. Bradsher reagent (CA 40: 57069) was refluxed 30 min. to give a mixture containing 16% VIII, 41.5% III, and 42.5% IV as compared with 6.5, 51, and 42, resp., after 1.5 hrs. of refluxing. The other II, when treated with Bradsher reagent, behaved similarly.
Bulletin de la Societe Chimique de France published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, Category: catalysis-chemistry.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia