Hydrochloric Acid → 1-Naphthalenecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-, methyl ester

反応式

[H-].[Na+].[O:3]=[C:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1.Cl.[C:15](=O)([O:18]C)[O:16][CH3:17]>>[C:15]([CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:12][CH2:13][C:4]1=[O:3])([O:16][CH3:17])=[O:18]

参加物

反応物 4

HCID 313Hydrochloric Acid

HCID 12021Dimethyl Carbonate

HCID 24758Sodium hydride

HCID 682662-Tetralone

生成物 1

HCID 5991311-Naphthalenecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-, methyl ester

実験手順

To a suspension of sodium hydride (60% oil dispersion, 4.8 g gross) in dimethyl carbonate (150 mL) stirring at room temperature under argon, was added 2-oxo-1,2,3,4-tetrahydronaphthalene (14.6 g). The resulting mixture was then refluxed for 30 min before cooling to 0° C. Once at the prescribed temperature and while maintaining inert atmosphere, 2.0 M aqueous hydrochloric acid solution (200 mL) was added slowly. Upon completion of the addition, the reaction mixture was extracted with ethyl acetate (three times). The combined extracts were dried over anhydrous magnesium sulfate and evaporated under vacuum to yield a residue. The residue was purified by silica gel chromatography eluting with 15% ethyl acetate in hexane to obtain the title compound (16.9 g).