Hydrochloric Acid → (1,1'-Biphenyl)-2,3'-diol

Temperature

80 °C

1692 g (18 mol) of phenol, 60.6 g (0.3 mol) of dodecylthiol and 420 g (3 mol) of dihydroisophorone (3,3,5-trimethylcyclohexan-1-one) are introduced into a stirring apparatus equipped with a stirrer, thermometer, reflux condenser and gas inlet pipe at 28°-30° C. Dry HCl gas is introduced into this solution over a period of 5 hours at 28°-30° C. The mixture is then left to react for about 10 h at 28°-30° C. When 95% of the ketone has been converted (examined by GC), 2.5 l of water are added to the reaction mixture and a pH value of 6 is adjusted by adding a 45% NaOH solution. The reaction mixture is stirred for one hour at 80° C. and then cooled to 25° C. The aqueous phase is decanted off and the remaining residue is washed with water at 80° C. The resulting crude product is filtered off and hot-extracted twice with n-hexane and twice with methylene chloride and then filtered. The residue is recrystallised twice from xylene.

1. customequipped with a stirrer
2. temperaturethermometer, reflux condenser and gas inlet pipe at 28°-30° C
3. waitThe mixture is then left
4. customto react for about 10 h at 28°-30° C
5. additionare added to the reaction mixture
6. temperaturecooled to 25° C
7. customThe aqueous phase is decanted off
8. washthe remaining residue is washed with water at 80° C
9. filtrationThe resulting crude product is filtered off
10. extractionhot-extracted twice with n-hexane and twice with methylene chloride
11. filtrationfiltered
12. customThe residue is recrystallised twice from xylene

ORD record

ord-44d3854980e7474cabb4290501e38724

Source dataset

uspto-grants-1993_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05227458