Ethanone, 1-(2,5-dichlorophenyl)- → 2,5-Dichloroethylbenzene

A suspension of mossy zinc (10 g) and mercuric chloride (0.5 g) in concd HCl (0.5 mL) and water (5 mL) was shaken for ~5 min. The aqueous layer was then decanted. To the residue was added concd HCl (7.5 mL) and water (7.5 mL) followed by 2',5'-dichloroacetophenone (3.106 g, 16.43 mmol) and the suspension was refluxed for 4 h during which time, hourly addition of concd HCl (90.5 mL) was carried out. The resulting suspension was cooled to room temperature and the aqueous layer was decanted. The residual solid was washed with ether (3×30 mL). The aqueous layer was extracted with ether (3×50 mL). The combined ether layer was washed with brine, dried over anhydrous Na2SO4, and removed under vacuum. The residue was dried further under vacuum to obtain 2.664 g crude product, which was purified on silica gel (hexane) to obtain 0.813 g (28%) pure (1H NMR) title compound as a colorless liquid; 1H NMR (DMSO-d6) δ1.23 (t, 3H, J=7.5 Hz), 2.73 (q, 2H, J=7.5 Hz), 7.09-7.27 (m, 3H).

1. customThe aqueous layer was then decanted
2. additionTo the residue was added concd HCl (7.5 mL) and water (7.5 mL)
3. customthe aqueous layer was decanted
4. washThe residual solid was washed with ether (3×30 mL)
5. extractionThe aqueous layer was extracted with ether (3×50 mL)
6. washThe combined ether layer was washed with brine
7. dry with materialdried over anhydrous Na2SO4
8. customremoved under vacuum
9. customThe residue was dried further under vacuum
10. customto obtain 2.664 g crude product, which
11. customwas purified on silica gel (hexane)

ORD record

ord-542ed5268d7d4c67afd4a6169b794c6b

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05631373