4-(4-Methoxy-3-methylphenyl)-4-oxobutanoic acid → 4-Methoxy-3-methylbenzenebutanoic acid

Participants

Reaction Steps

Zinc dust (40.0 g) was washed with HCl 10% and shaken for 2 min, and the water was decanted. HgCl2 (6.0 g) was then added, followed by water (60 mL) and concentrated HCl (2 mL). The mixture was shaken for 5 min, the water was decanted, and covered with water (30 mL) and concentrated HCl (70 mL). Toluene (20 mL) was added, followed by 4-(4-methoxy-3-methylphenyl)-4-oxobutyric acid (Compound 2, 11.7 g, 52.7 mmol). The resulting solution was refluxed vigorously for 24 h with addition of concentrated HCl (3×20 mL every 3 h). After being cooled down to room temperature, the two layers were separated, and the aqueous layer was washed three times with diethyl ether. The combined organic layers were washed with brine, dried over MgSO4, and filtered. The solvent was removed to give 10.7 g (98%) of the title compound as a light yellow solid.

Provenance & Evidence