Hydrochloric Acid → 3-Nitro-1-phenylpropan-1-one

Participants

Reaction Conditions

Reaction Steps

AlCl3 (12.0 g, 89.0 mmol) was added to 15 ml of methylene chloride and cooled to 0-5° C., following by addition of 3-nitropropanoyl chloride (11 g, 80 mmol). Octylbenzene (17.10 g, 89.0 mmol) in 40 ml of CH2Cl2 was dropwise added and the solution was stirred at room temperature under TLC monitoring. After reaction completion, the mixture was poured onto ice, acidified by addition of 2 M HCl to pH 2, and extracted with CH2Cl2. The combined organic extracts were washed again with 2 M HCl and water, dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to yield a solid that was recrystallized (hexanes) to give 3-nitro-1-phenylpropan-1-one (76%); mp 59-62° C., ESIMS 292 [M+H]+.

Provenance & Evidence