Fluorine-containing bisphenols, their preparation, their precursors and intermediates, and use of the fluorine-containing bisphenols
View Patent ↗This invention relates to 1,2-di(4-hydroxyaryl)tetrafluoroethanes of the general formula (I) wherein R are each, independently of one another, hydrogen, F, Cl, Br, I, CN, COOR 2 , C 1 –C 4 -alkyl, C 1 –C 4 -alkoxy, C 1 –C 4 -alkylthio, C 1 –C 4 -perfluoroalkyl, C 1 –C 4 -perfluoroalkoxy, C 1 –C 4 -perfluoroalkylthio, C 1 –C 4 -polyfluoroalkyl, C 1 –C 4 -polyfluoroalkoxy, or C 1 –C 4 -polyfluoroalkylthio, R 2 is C 1 –C 4 -alkyl, and n is an integer from 0 to 4. This invention further relates to the preparation of such compounds as well as to precursors and intermediates that can be used in their preparation.
1. A process for preparing a compound of formula (I)
Wherein
R are each, independently of one another, hydrogen, F, Cl, Br, I, CN, COOR 2 , C 1 –C 4 -alkyl, C 1 –C 4 -alkoxy, C 1 –C 4 -alkylthio, C 1 –C 4 -perfluoroalkyl, C 1 –C 4 -perfluoroalkoxy, C 1 –C 4 -perfluoroalkylthio, C 1 –C 4 -polyfluoroalkyl, C 1 –C 4 -polyfluoroalkoxy, or C 1 –C 4 -polyfluoroalkylthio,
R2 is C 1 –C 4 -alkyl, and
N is an integer from 0 to 4.
2. A process according to claim 1 wherein the ether cleavage of the compound of formula (VI) is carried out by hydrogenation or cleavage in acid medium.
3. A process according to claim 2 wherein hydrogenation is carried out when R 3 and/or R 4 is a benzyl radical or a substituted benzyl radical and cleavage in acid medium is carried out when R 3 and/or R 4 is isopropyl, tert-butyl, or cyclohexyl.
4. A process for preparing a compound of formula (I)
wherein
R are each, independently of one another, hydrogen, F, Cl, Br, I, CN, COOR 2 , C 1 –C 4 -alkyl, C 1 –C 4 -alkoxy, C 1 –C 4 -alkylthio, C 1 –C 4 -perfluoroalkyl, C 1 –C 4 -perfluoroalkoxy, C 1 –C 4 -perfluoroalkylthio, C 1 –C 4 -polyfluoroalkyl, C 1 –C 4 -polyfluoroalkoxy or C 1 –C 4 -polyfluoroalkylthio,
R 2 is C 1 –C 4 -alkyl, and
n is an integer from 0 to 4,
comprising
(1) reacting a benzotrichloride of formula (II)
wherein
R and n are as defined for formula (I), and
X is a halogen or pseudohalogen,
in the presence of copper and in a tertiary amine as solvent,
(2) reacting the product of step (1) with anhydrous hydrofluoric acid,
(3) carrying out an etherification of the product of step (2) with an alcohol of the formula R 3 OH and/or an alcohol of the formula R 4 OH,
wherein R 3 and R 4 are identical or different and are each benzyl, substituted benzyl, benzhydryl, substituted benzhydryl, isopropyl, tert-butyl, or cyclohexyl, and
(4) carrying out an ether cleavage on the product of step (3) to give the compound of formula (I).