Isobutyric Acid → 2,2-Dimethyldodecanoic acid

Isobutyric acid (13.9 ml) was added dropwise to a mixture of 21.1 ml of 62.5% sodium hydride, 93.8 ml of diisopropylamine and 150 ml of tetrahydrofuran (THF) at 30° C. or lower. After refluxing the mixture for 30 minutes, to the mixture was added 31.0 ml of a 1.6M n-butyl lithium-hexane solution at 10° C. or lower and the mixture was stirred for 15 minutes at the same temperature and for 2 hours at room temperature. At 10° C. or lower, 5.76 g of 1-bromodecane was added dropwise to the mixture. The mixture was stirred at the same temperature for one hour and then at room temperature overnight. After adding 300 ml of ice water, the reaction mixture was washed with diethyl ether, and the aqueous layer was adjusted to pH=1 with conc. hydrochloric acid and extracted with isopropyl ether. After the extract was washed and dried, the solvent was removed under reduced pressure to give 2.36 g of 2,2-dimethyllauric acid (state: pale yellow oily product).

1. temperatureAfter refluxing the mixture for 30 minutes
2. additionto the mixture was added 31.0 ml of a 1.6M n-butyl lithium-hexane solution at 10° C.
3. stirringThe mixture was stirred at the same temperature for one hour
4. customat room temperature
5. customovernight
6. washthe reaction mixture was washed with diethyl ether
7. extractionextracted with isopropyl ether
8. washAfter the extract was washed
9. customdried
10. customthe solvent was removed under reduced pressure

ORD record

ord-19914657285e453ea802ddb2b2f36da2

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05849732