Thionyl Chloride → 2-(1-Chloro-2-methyl-2-nitropropyl)naphthalene

Participants

Reaction Steps

To 2-methyl-1-(naphthalen-2-yl)-2-nitropropanol (1.23 g) obtained in Step 3 was added thionyl chloride (3.1 ml), and the resulting mixture was heated under reflux for 1 hr, and stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure and the residue thus obtained was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=93:7). Recrystallization from a solution of n-hexane:ethyl acetate=4:1, yielded title compound (776 mg).

Provenance & Evidence