Hydrogen Peroxide → HCID 13367858, compound

Temperature

-70 °C

To a solution of 24 ml of a 1M solution of lithium tri(sec-butyl)borohydride in tetrahydrofuran at -70° C. was added dropwise 3.49 g of 5,7,7-trimethyl-6-oxabicyclo[3.2.1]octan-4-one in 3 ml of tetrahydrofuran. The resulting solution was stirred under nitrogen for one hour at -70° C. and one hour at room temperature. Then while controlling the temperature at 0° C., the following were successively added: 2.6 ml of water, 5.2 ml of ethanol, 19.2 ml of 10% sodium hydroxide solution and dropwise 8.5 ml of 30% hydrogen peroxide solution. The resulting reaction mixture was stirred for one hour at 25° C., then saturated with solid potassium carbonate and extracted four times with 50 ml portions of a 1:1 solvent mixture of diethyl ether and tetrahydrofuran. The combined organic extracts were washed with 50 ml of saturated aqueous sodium chloride, dried (Na2SO4) and concentrated in vacuo to leave 6.44 g of an opaque, colorless oil. Kugelrohr distillation of the oil gave 3.13 g of the desired product as a colorless oil, b.p. 71° C. (0.35-0.15 mm), predominate (4:1) in the endo versus exo alcohol form.

1. customat 0° C.
2. additionthe following were successively added
3. customThe resulting reaction mixture
4. stirringwas stirred for one hour at 25° C.
5. extractionsaturated with solid potassium carbonate and extracted four times
6. additionwith 50 ml portions of a 1:1 solvent mixture of diethyl ether and tetrahydrofuran
7. washThe combined organic extracts were washed with 50 ml of saturated aqueous sodium chloride
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated in vacuo
10. customto leave 6.44 g of an opaque, colorless oil
11. distillationKugelrohr distillation of the oil

ORD record

ord-ff34666ee55749cfa395ff11236acf0c

Source dataset

uspto-grants-1985_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04536586