Hydrochloric Acid → 4-(5-Chloro-2-hydroxyphenyl)-4-oxobutanoic acid

Temperature

5 °C

A dry flask was charged with 650 ml. each of nitrobenzene and sym-tetrachloroethane, 104 g. (1.04 moles) succinic anhydride and 130 g. (0.913 mole) p-chloroanisole. The mixture was stirred at 5° C and 276 g. (2.07 moles) of anhydrous AlCl3 was added portionwise over a 90 minute period such that the temperature did not exceed 10° C. The resulting mixture was stirred under nitrogen for 5 days at 7° C and then poured into a mixture of 1 kg. of ice and 176 ml. concentrated hydrochloric acid. The thus quenched mixture was steam distilled until all organic solvents were removed. The residual aqueous-oil combination was cooled to 20° C whereupon the oil phase crystallized. The aqueous supernate was then drawn off and one liter of methylene chloride was added to the remaining crystallized solid mass. The resulting slurry was warmed at 25° C with stirring, and then filtered, and the filtered-off solids washed with CH2Cl2. Upon drying of the washed solids, 84.4 g. of 3-(5-chloro-2-hydroxybenzoyl) propionic acid, m.p. 178°-182° C., was obtained.

1. additionA dry flask was charged with 650 ml
2. customdid not exceed 10° C
3. stirringThe resulting mixture was stirred under nitrogen for 5 days at 7° C
4. additionpoured into a mixture of 1 kg
5. distillationdistilled until all organic solvents
6. customwere removed
7. temperatureThe residual aqueous-oil combination was cooled to 20° C whereupon the oil phase
8. customcrystallized
9. additionone liter of methylene chloride was added to the
10. customremaining crystallized solid mass
11. temperatureThe resulting slurry was warmed at 25° C
12. stirringwith stirring
13. filtrationfiltered
14. washthe filtered-off solids washed with CH2Cl2
15. customUpon drying of the washed solids, 84.4 g

ORD record

ord-4081c3aeea6643a6a7ebf927213e3f9e

Source dataset

uspto-grants-1977_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04022791