Krollpfelffer, F. published the artcileRing closures in ¦Ã-arylbutyric acids to derivatives of l-ketotetrahydronaphthalene, Related Products of catalysis-chemistry, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1923), 620-32, database is CAplus.
The ¦Ã-arylbutyric acids were prepared by letting the corresponding ¦Ã-keto acids and 10 parts amalgamated Zn stand at least 2-3 hrs., with frequent shaking, under just enough 30% HCl to cover the Zn and then boiling vigorously 6-10 hrs. Although attempts to convert these acids into 1-keto-1,2,3,4-tetrahydronaphthalene (I) derivatives by direct elimination of H2O between the side chain and the nucleus by means of concd, H2SO4 were not successful in all cases, it may be said in general that their tendency to undergo such a condensation is quite pronounced. PhCH2CH2CH2C02H (obtained in 80% yield), heated 3 hrs. on the H2O bath with 5 parts concentrated H2SO4 gives 50% I, b13 127¡ã. From 15 g. p-MeC6H4(CH2)3CO2H (obtained in 80% yield) is obtained 9 g. of the 7-Me derivative of I, m. 32.5-3.5¡ã; semicarbazone, m. 224-5¡ã. The ketone (5 g.), reduced by Clemmensen’s method, gives 2 g. 2-methyl-5,6,7,8-tetrahydronaphthalene, b. 224-6¡ã, and with Br in CS2 yields the 7-methyl-2-bromo derivative of I, m. 80.5¡ã, which produces severe burns on the skin and 9 g. of which, boiled 1 hr. with 50 g. PhNEt2, regenerates about 1 g. of the Br-free ketone and yields 2 g. 7-methyl-I-naphthol, b12. 158-9¡ã, m. 109¡ã, couples with diazotized P-O2NC6H4NH2 in alk. solution to a blue dye changing to red with acids. p- EtC6H4COCH2CH2CO2H, obtained in 70 g. yield from 60 g. succinic anhydride and 100 g. PhEt with AlCl3 in C6H6, m. 98-9¡ã. ¦Ã-p-Ethylphenylbutyric acid, m. 69-70¡ã, gives 50-5% of the 7-Et derivative of I, b12 152-3¡ã, slowly becomes brown-red in the air; semicarbazone, m. 223-5¡ã. Reduction of the ketone gives 2-ethyl-5,6,7,8-tetrahydronaph- thalene, b. 245-6¡ã. 2,4-Me2C6H3COCH2CH2CO2H, m. 111-2¡ã; the Me2C6H3(CH2)3– CO2H, m. 71¡ã, gives 10-5 % of the 5,7-Me2 derivative of I, m. 49-50¡ã, the small yield being due to sulfonation of the xylylbutyric acid. The ketone, which b14 180-2¡ã, is obtained in 40% yield from Me2C6H3COCl heated in vacuo at 150¡ã until the evolution of HCl ceases; semicarbazone, m. 234-5¡ã. ar-I,3-Dimethyltetralin (2.5 g. from 5 g. of the ketone with amalgamated Zn and HCl), b. 250-2¡ã. ¦Â-2-Tetroylpropionic acid (60 g. from 50 g. succinic anhydride and 100 g. tetralin with AlCl3 in C6H6), m. 121-2¡ã. ¦Â-2-Tetralyl- butyric acid, m. 49-50¡ã, gives 75% 1-ketooctahydroanthracene (“octhracenone,” Schroeter, C. A. 15, 525), b13 202¡ã, m. 46-7¡ã; semicarbazone, m. 252-3¡ã; 2-Br derivative, m. 110¡ã, produces severe burns on the skin and with PhNEt2 in part regenerates the Br-free ketone and in part forms 5,6,7,8-tetrahydro-I-anthrol, m. 124¡ã, becomes brown in the air, couples with diazotized P-O2NC6H4NH2 to a violet dye which is not fast to acids. ¦Â-¦Á’- Naphthoylisosuccinic acid, from CH2(CO2Et)2 refluxed in C6H6 with Na and then with ¦Á-C10H7COCH2Br, decomposes 158¡ã, with loss of CO2, 10 g. giving 5 g. of ¦Â-¦Á’-naphthoylpropionic acid, m. 131-2¡ã. ¦Ã-p-Methoxyphenylbutyric acid, m. 59-60¡ã, gives with H2SO4 only an easily soluble SO3H acid, but vacuum distillation of its chloride gives the 7-MeO derivative of I, m. 60-1¡ã; semicarbazone, m. 222-4¡ã. ¦Â-Benzoyl-¦Á-methylpropionic acid (50 g. from 60 g. pyrotartaric anhydride and AlCl3 in C6H6, m. 139-40¡ã. PhCH2– CH2CHMeCO2H, b15 174¡ã; anilide, m. 140¡ã. 2-Me derivative of I (2 g. from 5 g. of the above acid), b15 132¡ã, slowly turns brown in the air; semicarbazone, formed exceedingly slowly (3 days), m. 199-201¡ã. Below are given, resp., t¡ã, d4t and n for ¦Á, D, ¦Â and ¦Ã at t¡ã for the derivatives of I: ac-2-Me, 20.9¡ã, 1.0600, 1.54669, 1.55154, 1.56542, 1.57764; 7-Me, 35.0¡ã, 1.0569, 1.55168, 1.55674, 1.57160, 1.58479; 7-Et, 17.2¡ã, 1.0556, 1.55478, 1.55988, 1.57454, 1.58752; 5,7-Me2, 15.5¡ã, 1.0654, 1.55986, 1.56496, 1.57971, 1.59284. Derivatives of tetrahydronaphthalene: ar-2-Me, 15.1¡ã, 0.9541, 1.53316, 1.53719, 1.54907, 1.55897; ar-2-Et, 17.6¡ã, 0.9499, 1.53072, 1.53474, 1.54627, 1,55594; ar-1,3-Me2, 21.0¡ã, 0.9589, 1.53683, 1.54094, 1.55287.
Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 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, Related Products of catalysis-chemistry.
Referemce:
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Catalysis – Wikipedia