165. Syntheses in the phenanthrene series. Part X. 8-Methoxy-1-methylphenanthrene

Lockett, J.; Short, W. F.

doi:10.1039/jr9390000787

Cited by 11 publications

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“…87-88°; literature m.p. 89-89.5° ( 14)] by recrystallization from petroleum-ether. The semicarbazone of 5-methoxy-atetralone melted at 249-250°in agreement with the literature (14).…”

Section: Methodsmentioning

confidence: 99%

REDUCTIONS WITH NICKEL-ALUMINUM ALLOY AND AQUEOUS ALKALI. PART VI. NAPHTHALENE AND ITS SUBSTITUTION PRODUCTS¹

Papa¹,

Schwenk²,

Breiger³

1949

J. Org. Chem.

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In a previous publication (1) from these laboratories, the displacement of sulfonic acid groups by the action of a nickel-aluminum alloy in aqueous alkali was reported. In the case of naphthalene sulfonic acids, simultaneous reduction to tetrahydronaphthalenes accompanied hydrogenolysis of the sulfonic acid groups. This paper describes the results of our studies on the application of the Raney alloy reduction procedure to a variety of mono-and di-substituted naphthalene compounds.The hydrogenation of naphthalene and naphthalene derivatives to the corresponding tetrahydro and decahydro compounds has been the subject of many investigations. The classical studies of Bamberger (2) on the reduction of naphthalene derivatives by means of sodium and alcohols established the marked difference in reactivity of the substituted and unsubstituted rings of the naphthols. While -naphthol reduces almost exclusively in the unsubstituted ring to give the phenolic, or-a-tetralol (I), /3-naphthol reduces to the alcohol, ac-ß-

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“…87-88°; literature m.p. 89-89.5° ( 14)] by recrystallization from petroleum-ether. The semicarbazone of 5-methoxy-atetralone melted at 249-250°in agreement with the literature (14).…”

Section: Methodsmentioning

confidence: 99%

REDUCTIONS WITH NICKEL-ALUMINUM ALLOY AND AQUEOUS ALKALI. PART VI. NAPHTHALENE AND ITS SUBSTITUTION PRODUCTS¹

Papa¹,

Schwenk²,

Breiger³

1949

J. Org. Chem.

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“…The required 1 -iodo-7-methoxynaphthalene7 (10) was prepared from 7 -methoxy-1 -tetralone8 via the oxime which on treatment with acetic anhydride and PPA at 65-70 °C for 6 min yielded 1 -acetylamino-7 -methoxynaphthalene in 85% yield. This intramolecular oxidation-reduction reaction occurred much more readily than the conversion of the oxime of 1-tetralone to 1 -acetylaminonaphthalene, which required9 heating for 30 min at 80 °C.…”

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confidence: 99%

Syntheses of 1-, 2-, 3-, 4-, 6-, 9-, and 10-hydroxy-7,12-dimethylbenz[a]anthracenes

Newman¹,

Khanna²,

Kanakarajan³

et al. 1978

J. Org. Chem.

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“…The hydrobromic acid-acetic acid reagent has occasionally been used to remove acyl groups from aromatic hydroxyor methoxyketones (Konigs 1900;Kenner 1935Kenner , 1936. Bond-fission is sometimes accompanied by ring-fission as in the formation of y-($methoxy-1-naphthyl)butyric acid from 4-methoxy-7-oxo-cyclohepta-[dejnaphthalene (Lockett and Short 1939). Occasionally fission can be effected by hydrochloric acid and acetic acid as in the breakdown of 6-methoxy-2-(2,4,6-trimethoxybenzoyl)coumaran-3-one to 1,3,5-trimethoxybenzene (Bryant and Haslam 1967).…”

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XVI.—The Fission of Aromatic Ketones

Campbell

Thomson

1970

Proc. Sect. A, Math. phys. sci.

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SummaryThe acyl groups in aromatic ketones with hydroxyl or methoxyl groups in the ortho or para positions are readily removed by hydrobromic acid in acetic acid. The results are correlated with the fine structure of the parent hydrocarbons. 5,8-Dimethoxy-I-tetralone and 1,3-dihydroxyxanthone fail to undergo ring-fission with the reagent. The mechanism is discussed and it seems probable that fission occurs by direct proton attack at nucleophilic carbon atoms bearing the acyl groups.

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165. Syntheses in the phenanthrene series. Part X. 8-Methoxy-1-methylphenanthrene

Cited by 11 publications

References 0 publications

REDUCTIONS WITH NICKEL-ALUMINUM ALLOY AND AQUEOUS ALKALI. PART VI. NAPHTHALENE AND ITS SUBSTITUTION PRODUCTS¹

REDUCTIONS WITH NICKEL-ALUMINUM ALLOY AND AQUEOUS ALKALI. PART VI. NAPHTHALENE AND ITS SUBSTITUTION PRODUCTS¹

Syntheses of 1-, 2-, 3-, 4-, 6-, 9-, and 10-hydroxy-7,12-dimethylbenz[a]anthracenes

XVI.—The Fission of Aromatic Ketones

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165. Syntheses in the phenanthrene series. Part X. 8-Methoxy-1-methylphenanthrene

Cited by 11 publications

References 0 publications

REDUCTIONS WITH NICKEL-ALUMINUM ALLOY AND AQUEOUS ALKALI. PART VI. NAPHTHALENE AND ITS SUBSTITUTION PRODUCTS1

REDUCTIONS WITH NICKEL-ALUMINUM ALLOY AND AQUEOUS ALKALI. PART VI. NAPHTHALENE AND ITS SUBSTITUTION PRODUCTS1

Syntheses of 1-, 2-, 3-, 4-, 6-, 9-, and 10-hydroxy-7,12-dimethylbenz[a]anthracenes

XVI.—The Fission of Aromatic Ketones

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REDUCTIONS WITH NICKEL-ALUMINUM ALLOY AND AQUEOUS ALKALI. PART VI. NAPHTHALENE AND ITS SUBSTITUTION PRODUCTS¹

REDUCTIONS WITH NICKEL-ALUMINUM ALLOY AND AQUEOUS ALKALI. PART VI. NAPHTHALENE AND ITS SUBSTITUTION PRODUCTS¹