Hydrochloric Acid → 1-(2-Ethyl-butyl)-cyclohexanecarboxylic acid

A suspension of 60% sodium hydride (980 mg) in tetrahydrofuran (80 ml) was stirred at room temperature and a tetrahydrofuran solution (10 ml) containing cyclohexanecarboxylic acid (3.00 g) was added dropwise thereto. After completion of addition, a mixture was stirred for 1 hour and cooled to 0° C., followed by adding a cyclohexane solution (18.7 ml) containing 1.5M lithium isopropylamide dropwise thereto. Then, after stirring at room temperature for 1.5 hours and cooling to 0° C., a tetrahydrofuran solution (10 ml) containing 1-bromo-2-ethylbutane (4.64 g) was added dropwise thereto. The solution was gradually warmed to room temperature and stirred overnight. Water and a 10% hydrochloride solution were added to this reaction solution and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After drying, the resulting solution was concentrated to obtain 1-(2-ethylbutyl)cyclohexanecarboxylic acid (3.17 g, yields 64%).

1. additionwas added dropwise
2. additionAfter completion of addition
3. stirringa mixture was stirred for 1 hour
4. temperaturecooled to 0° C.
5. stirringThen, after stirring at room temperature for 1.5 hours
6. temperaturecooling to 0° C.
7. additionwas added dropwise
8. temperatureThe solution was gradually warmed to room temperature
9. stirringstirred overnight
10. extractionthe solution was extracted with ethyl acetate
11. washThe organic layer was washed with saturated brine
12. dry with materialdried over anhydrous sodium sulfate
13. customAfter drying
14. concentrationthe resulting solution was concentrated

ORD record

ord-c2c0fac838bf4258976e0415b4d7cd12

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000045B2