Dichloroacetic Acid → Benzeneacetic acid, 4-methoxy-alpha-(4-methoxyphenyl)-

To neat morpholine (43.56 g, 0.5 mol) was added dichloroacetic acid (12.89 g, 0.1 mol) portionwise under argon, with ice bath. When the addition was finished, the ice bath was removed and the reaction was allowed to stand at ambient temperature for 16 hours. The reaction mixture was dissolved in a mixed solvent of 120 mL acetic acid and 12 mL H2O and was stirred at room temperature until it was clear. To the reaction was then added anisole (43.2 g, 0.4 mol) followed by 100 mL concentrated H2SO4 with ice bath keeping temperature less then 25° C. The reaction was stirred at room temperature for 16 hours and warmed to 60° C. for 3 hours. The reaction mixture was poured over the ice and was extracted with CHCl3. The CHCl3 layer was then washed with 1N NaOH then filtered. The aqueous solution was acidified with HCl to give a cloudy solution which crystallized upon standing at room temperature for 64 hours. The crystalline solid was filtered and rinsed with H2O to give the acid (15.2 g, 55%).

1. additionWhen the addition
2. customthe ice bath was removed
3. dissolutionThe reaction mixture was dissolved in a mixed solvent of 120 mL acetic acid and 12 mL H2O
4. custom25° C
5. stirringThe reaction was stirred at room temperature for 16 hours
6. temperaturewarmed to 60° C. for 3 hours
7. extractionwas extracted with CHCl3
8. washThe CHCl3 layer was then washed with 1N NaOH
9. filtrationthen filtered
10. customto give a cloudy solution which
11. customcrystallized
12. waitupon standing at room temperature for 64 hours
13. filtrationThe crystalline solid was filtered
14. washrinsed with H2O

ORD-Eintrag

ord-c54b7cc3cd9846589412d51014e564ac

Quelldatensatz

uspto-grants-1998_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05789197