4-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acid → 4-[3-(Methyloxy)-3-oxopropyl]-1-naphthalenecarboxylic acid
Reaction equation
[CH3:1][O:2][C:3](=[O:19])/[CH:4]=[CH:5]/[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1Participants
4
Procedure
4-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acid (for example as prepared for Intermediate 5) (4 g, 5.09 mmol) in 500 mL ethanol was hydrogenated over palladium on carbon (10 wt %, 1 g) for about 2 h. The catalyst was removed by filtration through Celite, the solvent evaporated and the resultant solid left overnight under vacuum to afford the title compound (3.8 g). ES+ve m/z 258 (M+H)+.