Sodium Sulfite → 1-(Benzyloxy)-3-chloropropan-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzyloxy-3-chloro-propan-2-ol (10.0 g, 50.0 mmol) [prepared according to Journal of Organic Chemistry (1990), 55, 4897] in ethyl acetate (125 mL) was added a solution of NaHCO3 (12.6 g, 150 mmol) and NaBr (5.66 g, 55.0 mmol) in water (75 mL). After cooling of the biphasic mixture to 0° C., 2,2,6,6-Tetramethyl-piperidin-1-yl)oxyl (“TEMPO”) (391 mg, 2.50 mmol) was added in one portion followed by dropwise addition of NaOCl (6 wt % in water, 85.4 mL, 75.0 mmol) to the vigorously stirred solution. After completion of the addition, stirring at 0° C. was continued for 30 min. Subsequently, a solution of aqueous Na2SO3 was added until the reaction mixture had completely discolored. Additional solid Na2SO3 was added to saturate the aqueous phase. The mixture was transferred to a separation funnel and the layers were separated. The organic layer was washed with brine (100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure (at 20° C.). The remaining oil was used without further purification. 1H NMR (400 MHz, CDCl3) 4.26 (s, 2H), 4.33 (s, 2H), 4.62 (s, 2H), 7.31-7.45 (m, 5H).

Provenance & Evidence