Sulfuric Acid → 1-Ethyl-4-trifluoromethylcyclohexanol

Temperatur

-5 °C

The inside of a reactor was sufficiently dried by vacuum heating, and the atmosphere inside the reactor was replaced with dry nitrogen. The reactor was charged with a Grignard reagent that was prepared in 350 ml of dehydrated tetrahydrofuran (dehydrated THF) using 9.7 g (0.40 mol) of a magnesium powder and 38.9 g (0.36 mol) of bromoethane 50 ml of a dehydrated THF solution of 49.8 g (0.30 mol) of 4-trifluoromethylcyclohexanone was added to the reactor over 15 minutes with stirring while cooling the solution at −5° C. using an ice bath. After increasing the temperature of the reactor to room temperature, the mixture was stirred for 2 hours. 500 ml of ice water and 100 ml of ice-cooled diluted sulfuric acid were then added to the mixture while sufficiently stirring the mixture. After separating the THF layer, the aqueous layer was extracted with diethyl ether to obtain an extract. The extract was combined with the THF layer, sequentially washed with a 5% sodium carbonate aqueous solution and water, and dried over sodium sulfate (desiccating agent). After removing sodium sulfate using a Buchner funnel, the organic solvent was evaporated. The residue was distilled under reduced pressure (30 mmHg). 1-Ethyl-4-trifluoromethylcyclohexanol was thus obtained (41.2 g (yield: 70%)).

1. customThe inside of a reactor was sufficiently dried by vacuum
2. temperatureheating
3. additionThe reactor was charged with a Grignard reagent that
4. customwas prepared in 350 ml of dehydrated tetrahydrofuran (dehydrated THF)
5. additionwas added to the reactor over 15 minutes
6. temperatureAfter increasing the temperature of the reactor to room temperature
7. stirringthe mixture was stirred for 2 hours
8. additionwere then added to the mixture
9. stirringwhile sufficiently stirring the mixture
10. customAfter separating the THF layer
11. extractionthe aqueous layer was extracted with diethyl ether
12. customto obtain an extract
13. washsequentially washed with a 5% sodium carbonate aqueous solution and water
14. dry with materialdried over sodium sulfate (desiccating agent)
15. customAfter removing sodium sulfate using a Buchner funnel
16. customthe organic solvent was evaporated
17. distillationThe residue was distilled under reduced pressure (30 mmHg)

ORD-Eintrag

ord-3eda108bfce74d3d871703601a0114d2

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08535871B2