Sodium Hydroxide → trans-4-Cyanocyclohexanecarboxylic acid

To the solution of methyl 4-cyanocyclohexylcarboxylate (470 mg, 2.81 mole) prepared according to the method described in J. Am. Chem. Soc., 82, 2547 (1960) in methanol (5 ml) was added 1N sodium hydroxide (2.8 ml) under ice-cooling, and the mixture was stirred overnight during which the temperature of the mixture was left rising up to room temperature. After the reaction mixture was concentrated, water was added. The resulting mixture was washed with ether and acidified with 5N hydrochloric acid. After extracted thrice with chloroform, the mixture was dried with anhydrous magnesium sulfate. After the inorganic salt was removed by filtration, the filtrate was concentrated under reduced pressure to give 362 mg of the title compound as a colorless crystal (yield, 84%).

1. temperaturecooling
2. waitwas left
3. customrising up to room temperature
4. concentrationAfter the reaction mixture was concentrated
5. additionwater was added
6. washThe resulting mixture was washed with ether
7. extractionAfter extracted thrice with chloroform
8. dry with materialthe mixture was dried with anhydrous magnesium sulfate
9. customAfter the inorganic salt was removed by filtration
10. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-b83b294c528d4ea3914bbf02d1a845de

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05698692