Acetic Acid → Ethyl 4-oxocyclohexanecarboxylate

To a 3-L 3-neck flask equipped with a mechanical stirrer, a thermometer, and an addition funnel were added 50 g (292 mmol) of the compound of Formula 32.0 from Step 1, 33 mL (584 mmol) of acetic acid and 145 mL of commercial bleach (5.25% NaOCl). To the cooled reaction mixture, at 5° C., was added dropwise 479 mL of more bleach. The reaction was allowed to warm to room temperature for 1 hour and then was extracted with 3×400 mL ethyl acetate. The combined extract was washed with water, dried over MgSO4, and concentrated to give 49 g of crude 33.0 as an oil which was used without purification. The spectrum data are identical to that of literature (see Sanchez, I. H.; Ortega, A.; Garcia, G.; Larraza, M. I.; Flores, H. J. Synthetic comm. 1985, 15, 141).

1. customTo a 3-L 3-neck flask equipped with a mechanical stirrer
2. customTo the cooled reaction mixture
3. additionat 5° C., was added dropwise 479 mL of more bleach
4. extractionwas extracted with 3×400 mL ethyl acetate
5. extractionThe combined extract
6. washwas washed with water
7. dry with materialdried over MgSO4
8. concentrationconcentrated

ORD record

ord-40e7cc2e9b1c4a52a1628d48773bbb9a

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05648484