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

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.

1. washZinc dust (40.0 g) was washed with HCl 10%
2. customthe water was decanted
3. additionHgCl2 (6.0 g) was then added
4. stirringThe mixture was shaken for 5 min
5. customthe water was decanted
6. additionToluene (20 mL) was added
7. customthe two layers were separated
8. washthe aqueous layer was washed three times with diethyl ether
9. washThe combined organic layers were washed with brine
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. customThe solvent was removed

ORD record

ord-419f2dd248a14391b54b9d05fb87052a

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613917B1