Ethanol → 2-Oxocycloheptane-1-carbaldehyde

In an argon atmosphere, sodium hydride (60%; 55.2 g, 1.38 mol) was suspended in ether (2 L), and ethanol (2.5 mL) was added thereto at room temperature. Then, a liquid mixture of cycloheptanone (141 g, 1.26 mol) and ethyl formate (152 mL, 1.84 mol) was added dropwise to the mixture over 2 hours, and the resulting mixture was stirred at the same temperature for 20 hours. Ethanol (25 mL) was added to the reaction solution, subsequently water (1.2 L) was added, and the mixture was separated. The resultant was extracted with a 10% (w/v) aqueous solution of sodium hydroxide, and then the aqueous layers were combined and washed with ether. 15% (v/v) hydrochloric acid was added to the aqueous layer under ice cooling to adjust the aqueous layer to pH 3 to 4, and then the mixture was extracted twice with ether, washed with saturated solution of sodium chloride, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and thus the title compound (174 g, 99%) was obtained as a pale orange oil.

1. customat room temperature
2. additionwas added dropwise to the mixture over 2 hours
3. additionwas added
4. customthe mixture was separated
5. extractionThe resultant was extracted with a 10% (w/v) aqueous solution of sodium hydroxide
6. washwashed with ether
7. addition15% (v/v) hydrochloric acid was added to the aqueous layer under ice cooling
8. extractionthe mixture was extracted twice with ether
9. washwashed with saturated solution of sodium chloride
10. dry with materialdried over anhydrous sodium sulfate
11. customThe solvent was evaporated under reduced pressure

ORD record

ord-73a46534609242d78d0d44e5be22c1fc

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875625B2