Hydrochloric Acid → HCID 55115836, compound

Temperature

40 °C

In a nitrogen atmosphere, a solution prepared by dissolving 75.85 g of 3,5-difluorobromobenzene in 150 mL of THF was added at a rate that caused gentle reflux to a solution prepared by suspending 10.03 g of magnesium in 50 mL of THF, followed by stirring at 40° C. for 1 hour. After the resultant mixture was allowed to cool to room temperature, a solution prepared by dissolving 60.62 g of 4-propylcyclohexanone in 120 mL of THF was added to the mixture at such a rate that the inside temperature did not exceed 35° C., followed by stirring at room temperature for 2 hours. Then, 10% hydrochloric acid was added until the reaction system became acidic, and an organic layer was separated from the mixture. Further, an aqueous layer was subjected to extraction with toluene, and the toluene extract was combined with organic layer and washed with saturated brine. The resultant mixture was dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure to yield 132 g of crude 1-(1-hydroxy-4-propylcyclohexyl)-3,5-difluorobenzene.

1. customIn a nitrogen atmosphere, a solution prepared
2. additionwas added at a rate that
3. temperaturecaused gentle reflux to a solution
4. customprepared
5. temperatureto cool to room temperature
6. customa solution prepared
7. additionwas added to the mixture at such a rate that the inside temperature
8. customdid not exceed 35° C.
9. stirringby stirring at room temperature for 2 hours
10. customan organic layer was separated from the mixture
11. extractionFurther, an aqueous layer was subjected to extraction with toluene
12. extractionthe toluene extract
13. washwashed with saturated brine
14. dry with materialThe resultant mixture was dried
15. additionby adding sodium sulfate
16. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-61e6c04a19bd43c88f91ae37b025735f

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916718B2