Dimethylformamide → 2-Chlorocyclohex-1-enecarbaldehyde

Participants

Reaction Steps

Phosphoryl trichloride (125 g, 815 mmol) was added dropwise into a flame-dried bottom flask containing N,N-dimethylformamide (74.5 g, 1019 mmol) at 0° C. with stirring. After addition, the mixture was warmed to ambient temperature for 30 min, and re-cooled to 0° C. before the dropwise addition of cyclohexanone (50 g, 509 mmol). The mixture was warmed to room temperature for 12 h. The reaction was poured over ice and quenched with NaHCO3. Once neutralized, the mixture was extracted with ethyl acetate (100 mL×3) and washed with water and brine. The organic phase was dried, filtered, and concentrated to afford the product (160 g, 87% yield). 1H NMR: (CDCl3, 400 MHz) δ 1.74˜1.75 (m, 2H), 1.76˜1.78 (m, 2H), 2.24˜2.27 (m, 2H), 2.53˜2.59 (m, 2H), 7.25 (s, 1H).

Provenance & Evidence