Hydrogen Peroxide → HCID 19753535, compound

Temperature

-78 °C

3-(3-methoxy-3-methylbut-1-yl)cyclohexanone (1.4 g, 0.0051 mol) was dissolved in tetrahydrofuran (10 mL) and cooled to -78° C. under a nitrogen atmosphere with stirring. A solution of lithium tri-sec-butylborohydride (6.1 mL of a 1M solution of tetrahydrofuran, 0.0061 mol) was added. The mixture was allowed to come to 20° C. over 16 hours and 10% NaOH (aq, 4.0 mL) was added, followed by 30% hydrogen peroxide (aq, 4.0 mL). The mixture was extracted with hexane. The extracts were dried (Na2SO4) and concentrated to the residue which was purified by bulb to bulb distillation (air bath temp 175° C., 0.1 mm Hg) to yield 3-(3-methoxy-methylbut-1-yl)cyclohexanol as a mixture of diastereoisomers in the ratio of 94:6 (0.7 g). NMR(CDCl3)δ1.1(s,6H), 1.2-1.8(m,13H), 3.2(s,3H), 4.1(brs,1H). IR(neat) 3410, 2990, 2960, 2870, 1460, 1370, 1110, 1090, 980 cm-1. MS(m/e) 43, 73, 109, 124, 143, 181, 201, 214.

1. extractionThe mixture was extracted with hexane
2. dry with materialThe extracts were dried (Na2SO4)
3. concentrationconcentrated to the residue which
4. distillationwas purified by bulb to bulb distillation (air bath temp 175° C., 0.1 mm Hg)

ORD record

ord-fc00aaf979ef4e82b64e5be60045c3e7

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04891447