Potassium Carbonate → 3-(4-Chlorophenyl)-5-benzofuranacetic acid

In 200 ml. of glyme are placed 28.6 g. (0.159 mole) of ethyl (4-hydroxyphenyl)acetate, 37.2 g. (0.159 mole) of 4-chloro-α-bromoacetophenone and 28.6 g. of potassium carbonate. The mixture is heated at its reflux temperature for five hours, then diluted with water and diethyl ether. The ether layer is washed with water, cold 0.5 N sodium hydroxide solution and saturated sodium chloride solution and treated with decolorizing charcoal, then dried. The solution is evaporated to provide a residue which is recrystallized from methanol yielding 24.4 g. of yellow crystals of condensation product, m.p. 87°-92° C. This product is mixed with 165 g. of polyphosphoric acid and heated at 110° C. for 1.5 hours. The mixture is poured into ice and water. This mixture is extracted with diethyl ether. The ether layer is washed with water and saturated sodium chloride solution, then dried. Evaporation provides 20.7 g. of ethyl 3-(4-chlorophenyl)-5-benzofuranacetate. This ester is hydrolyzed in 210 ml. of ethanol with 21 ml. of water and 20.7 g. of sodium hydroxide by heating at reflux for two hours. The solution is evaporated, and the residue is partitioned into water and diethyl ether. The water layer is poured into cold dilute hydrochloric acid to provide a yellow, gummy solid. The solid is dissolved in diethyl ether. The ether layer is washed with water and saturated sodium chloride solution, then dried. Evaporation provides a solid which is recrystallized twice from aqueous ethanol, then from benzene to yield 3-(4-chlorophenyl)-5-benzofuranacetic acid, m.p. 136°-140° C.

1. temperatureThe mixture is heated at its
2. temperaturereflux temperature for five hours
3. washThe ether layer is washed with water, cold 0.5 N sodium hydroxide solution and saturated sodium chloride solution
4. additiontreated with decolorizing charcoal
5. customdried
6. customThe solution is evaporated
7. customto provide a residue which
8. customis recrystallized from methanol yielding 24.4 g
9. customof yellow crystals of condensation product, m.p. 87°-92° C
10. additionThis product is mixed with 165 g
11. extractionThis mixture is extracted with diethyl ether
12. washThe ether layer is washed with water and saturated sodium chloride solution
13. customdried
14. customEvaporation
15. customprovides 20.7 g
16. temperatureat reflux for two hours
17. customThe solution is evaporated
18. customthe residue is partitioned into water and diethyl ether
19. additionThe water layer is poured into cold dilute hydrochloric acid
20. customto provide a yellow, gummy solid
21. washThe ether layer is washed with water and saturated sodium chloride solution
22. customdried
23. customEvaporation
24. customprovides a solid which
25. customis recrystallized twice from aqueous ethanol

ORD-Eintrag

ord-3b8b7def5891429c9451c857be5c8700

Quelldatensatz

uspto-grants-1979_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04153619