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ChemicalBook CAS DataBase List Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate
116047-26-8

Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate synthesis

5synthesis methods
Methanol

67-56-1

8-OXO-5,6,7,8-TETRAHYDRO-NAPHTHALENE-2-CARBOXYLIC ACID

89781-52-2

Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

116047-26-8

Intermediate VIII: Steps for the synthesis of methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate: Step a) Preparation of methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate: to a methanolic solution of 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (16 g, 0.084 mol) was added sulfoxide chloride (23 g, 0.2 mol). The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate (200 mL), the organic layer was washed with 10% aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate 16 g (94% yield) as a liquid. Thin layer chromatography (TLC) conditions: chloroform/methanol (9/1, v/v), Rf = 0.9.

201230-82-2 Synthesis
carbon monoxide

201230-82-2
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Methanesulfonic acid, 1,1,1-trifluoro-, 5,6,7,8-tetrahydro-8-oxo-2-naphthalenyl ester

144464-65-3
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Yield:116047-26-8 95%

Reaction Conditions:

with 1,3-bis-(diphenylphosphino)propane;triethylamine;palladium diacetate in N,N-dimethyl-formamide;Carbonylation;

References:

Murphy, Paul V.;Hubbard, Rod E.;Manallack, David T.;Wills, Ruth E.;Montana, John G.;Taylor, Richard J. K. [Bioorganic and Medicinal Chemistry,1998,vol. 6,# 12,p. 2421 - 2439]