Ozone → 1-Heptanol, 7-bromo-

Temperature

-50 °C

A solution of 8-bromo-1-octene (5.0 g, 26 mmol) in a mixture of 25 mL of MeOH and 5 mL of CH2Cl2 was cooled to -50° C. and treated with O3 until a blue color persisted (45 min) and then for an additional 10 min. The mixture, at -40° C., was purged with N2 for 10 min, allowed to warm to -20° C., under N2, and kept at -20° C. while 1.3 g (34 mmol) of sodium borohydride was added in portions over 30 min (evolution of H2 was evident at each addition). The mixture was stirred 30 min more at -20° C. and quenched with the dropwise addition of 20 mL of H2O. This mixture was stirred for 10 min, and extracted with hexane; the organic extracts were washed with water, then brine, dried (Na2SO4) and concentrated to give 3.65 g (72%) of 7-bromo-1-heptanol: NMR (CDCl3) δ1.44 (m, 9H), 1.85 (m, 2H), 3.41 (t, 2H), 3.65 (t, 2H).

1. custom(45 min)
2. customThe mixture, at -40° C., was purged with N2 for 10 min
3. temperatureto warm to -20° C., under N2
4. additionwas added in portions over 30 min (evolution of H2
5. additionwas evident at each addition)
6. customquenched with the dropwise addition of 20 mL of H2O
7. stirringThis mixture was stirred for 10 min
8. extractionextracted with hexane
9. washthe organic extracts were washed with water
10. dry with materialbrine, dried (Na2SO4)
11. concentrationconcentrated

ORD record

ord-c7e72cb43fb9441d907062c851cbb079

Source dataset

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05405997