3-Hydroxycycloheptanone → Cycloheptane-1,3-dione

To a 10°-20° C. solution of 20 g. (0.156 mole) of 3-hydroxycycloheptanone in 700 ml. of acetone was slowly added 54.9 ml. of 2.67 M Jone's reagent (0.146 mole). The mixture was stirred 15 minutes and then quenched by addition of 12 ml. of isopropanol. The reaction was filtered through diatomaceous earth and the filtrate concentrated on a rotovapor to about 100 ml. The residue was diluted with 300 ml. of saturated sodium chloride and then extracted with six 250 ml. portions of ether. The combined organic extract was washed with two 100 ml. portions of saturated sodium bicarbonate, dried over magnesium sulfate and evaporated under reduced pressure (aspirator) to yield an oil. Distillation of the crude oil gave 11.5 g. (58%) of the title compound as an oil.

1. customTo a 10°-20° C.
2. customquenched by addition of 12 ml
3. filtrationThe reaction was filtered through diatomaceous earth
4. concentrationthe filtrate concentrated on a rotovapor to about 100 ml
5. additionThe residue was diluted with 300 ml
6. extractionof saturated sodium chloride and then extracted with six 250 ml
7. extractionThe combined organic extract
8. washwas washed with two 100 ml
9. dry with materialportions of saturated sodium bicarbonate, dried over magnesium sulfate
10. customevaporated under reduced pressure (aspirator)
11. customto yield an oil
12. distillationDistillation of the crude oil
13. customgave 11.5 g

ORD record

ord-817a02c28ee54a85985a33081cc7c055

Source dataset

uspto-grants-1989_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04831059