Water → Hydrochloric Acid

Water (6 mL) was added to 111 mg (0.408 mmol) of mercury chloride (HgCl2) to dissolve therein, 4.00 g (6.12 mmol) of zinc powder was added to the solution and the resulting mixture was stirred at room temperature for 50 minutes. After removing the supernatant, the remained solid was washed once with water. To the material were gradually added water (6.0 mL), and then, conc. hydrochloric acid (5.0 mL), and further added acetic acid (2.4 mL), and finally 409 mg (1.82 mmol) of 8-(3-chloropropyl)-5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one obtained in (4) dissolved in toluene (2 mL) and ethanol (2 mL). The mixture was stirred at 115° C. overnight, and cooled up to room temperature. Toluene (20 mL) was added to the mixture and the resulting mixture was stirred at 30 minutes, and the organic layer was separated. The obtained organic layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate=20:1) to obtain 304 mg (1.44 mmol, Yield: 79.1%) of 7-(3-chloropropyl)-2-methoxybicyclo[4.2.0]octa-1,3,5-triene.

1. dissolutionto dissolve
2. customAfter removing the supernatant
3. washthe remained solid was washed once with water

ORD record

ord-c2aa654d7964416b954e5a717881f231

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07608563B2