6-Chlorohexanoyl chloride → HCID 54497828, compound

Participants

Reaction Steps

1,8 dichloro-3-octanone: A well stirred, ice-cooled solution of 30.35 g (179.6 mmol) of 6-chlorohexanoyl chloride in 300 ml of dry CCl4 was degassed with nitrogen for 1/2 hr. AlCl3 (26.34 g, 179.6 mmol) was added in portions, then ethylene was bubbled in at a rate so that no excess ethylene escaped from the reaction vessel. Ethylene was allowed to bubble through the reaction mixture at 0° C. for 2 hrs. and at ambient temperature overnight. The reaction mixture was poured into 800 ml ice-water and extracted with chloroform (2×400 ml). The combined chloroform extracted were washed with sat'd aq. NaHCO3 (500 ml), H2O (500 ml), sat'd NaCl (500 ml) and dried over MgSO4. After the removal of the solvent, 15.2 g (43%) of crude 1,8-dichlorooctanone was obtained, which was used without further purification. NMR(CDCl3): δ1.44 (6H, m, --CH2 --), δ2.34 (2H, t, ##STR19## J=3.0 Hz), δ2.85 (2H, t, ##STR20## J=3.0 Hz), δ3.52 (2H, t, --CH2Cl, J=3 Hz) δ3.74 (2H, t, --CH2Cl, J=3.0 Hz).

Provenance & Evidence