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

Temperatur

0 °C

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).

1. addition2,2,6,6-Tetramethyl-piperidin-1-yl)oxyl (“TEMPO”) (391 mg, 2.50 mmol) was added in one portion
2. additionAfter completion of the addition
3. concentrationto saturate the aqueous phase
4. customThe mixture was transferred to a separation funnel
5. customthe layers were separated
6. washThe organic layer was washed with brine (100 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure (at 20° C.)
10. customThe remaining oil was used without further purification

ORD-Eintrag

ord-fe0fe9f00f5e4c10817d47cf25ef3841

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09024019B2