Alexander, Elliot R. published the artcileMechanism of Chugaev and acetate thermal decompositions. II. cis- and trans-2-Methyl-1-tetralol, Synthetic Route of 1949-41-3, the publication is Journal of the American Chemical Society (1950), 3194-8, database is CAplus.
cf. C.A. 44, 7254a. Details are given of the preparation of BzCH2CHMeCO2H (60%), PhCH2CH2CHMeCO2H (85%), and 3, 4-dihydro-2-methyl-1(2H)-naphthalenone (I) (92%). Reduction of 10 g. I in 150 ml. 95% EtOH with 10 g. Na gives 2 g. crude trans-1,2,3,4-tetrahydro-2-methyl-1-naphthol (II), m. 74-5¡ã; if the filtrate from the recrystallization is added to another batch of I being reduced, the yield of II is 3-4 g.; 3,5-dinitrobenzoate, light yellow, m. 155-6¡ã. I (10 g.) in 40 ml. absolute EtOH, hydrogenated over 4 g. Raney Ni (9 hrs.) at room temperature and 45 lb./sq. in. and purified through the phenylurethan (m. 122-4¡ã, 67%), gives the cis isomer (III) of II, b0.2-0.3 90-4¡ã, nD20 1.5502. II yields 81% Me trans-1,2,3,4-tetrahydro-2-methyl-1-naphthylxanthate (IV), m. 58-9¡ã; cis isomer (V), m. 71-2¡ã, 17%. II acetate (VI), m. 61-2¡ã; III acetate (VII), b0.2-0.3 86-92¡ã, nD20 1.5192. Reduction of I over Cu chromite at 100¡ã and 1600 lb./sq. in. gives 2-methyl-3, 4-dihydronaphthalene (VIII), b0.6 63-5¡ã, nD20 1.5751, d2020 0.9837 (picrate, unstable, m. 70-4¡ã). V is stable at 98-100¡ã, whereas IV is rapidly decomposed, forming VIII. VII is much more stable than VI; VI gives VIII, whereas VII at 650¡ã gives 2-C10H7Me. The results are given as curves. These results are in agreement with the point of view that the Chugaev reaction and the simple thermal decomposition of acetates involve the intermediate formation of a transitory 6-membered ring with a cis-¦Â-H atom.
Journal of the American Chemical Society 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, Synthetic Route of 1949-41-3.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia