Phenol → 2-(Hexafluoro-2-hydroxy-2-propyl)phenol

Temperature

-35 °C

94.11 g (1000 mmol) of phenol and 166.02 g (100 mmol) of AlCl3 were initially charged in 1200 ml of 1,2-dichloroethane and cooled to −35° C. At this temperature, the precalculated amount of 166.02 g (1000 mmol) of hexafluoroacetone was metered in from a bomb. Subsequently, the reaction mixture was allowed to come to room temperature (20° C., RT) and stirred at RT for a further 36 h. The reaction flask was subsequently flushed with N2 and the offgas passed into a wash bottle containing water. For workup of the remaining reaction solution, 500 ml of water were added cautiously and the mixture was stirred well. Subsequently, the organic phase was removed, the aqueous phase was extracted with CH2Cl2 and dried over magnesium sulphate, and the solvent was removed on a rotary evaporator. As this was done, the residue crystallized out. For purification, the resulting crystals were slurried in n-hexane and filtered off, and 230 g (842 mmol, yield: 82.4% of theory) of a white, crystalline solid were obtained.

1. customto come to room temperature
2. custom(20° C., RT)
3. customThe reaction flask was subsequently flushed with N2
4. additioncontaining water
5. customFor workup of the remaining reaction solution, 500 ml of water
6. additionwere added cautiously
7. stirringthe mixture was stirred well
8. customSubsequently, the organic phase was removed
9. extractionthe aqueous phase was extracted with CH2Cl2
10. dry with materialdried over magnesium sulphate
11. customthe solvent was removed on a rotary evaporator
12. customthe residue crystallized out
13. customFor purification
14. filtrationfiltered off
15. custom230 g (842 mmol, yield: 82.4% of theory) of a white, crystalline solid were obtained

ORD record

ord-28fbc1e517e242ddbb6275578523354e

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08227626B2