Acetic Acid → Indoxyl acetate

Temperature

90 °C

Into a 500 mL round bottom flask was placed a solution of 3-iodo-1H-indole (23 g, 94.65 mmol) in acetic acid (300 mL). To the mixture was added CH3COOAg (31.6 g, 189.22 mmol). The resulting solution was allowed to react, with stirring, for 1 hour while the temperature was maintained at 90° C. in a bath of oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:1). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was dissolved with 100 mL of ethyl acetate. The resulting mixture was washed 2 times with 100 mL of NaCl(aq.). The final product was purified by recrystallization from MeOH/H2O in the ratio 2:3. This resulted in 8.5 g (41%) of 1H-indol-3-yl acetate as a dark purple solid.

1. customInto a 500 mL round bottom flask was placed
2. additionTo the mixture was added CH3COOAg (31.6 g, 189.22 mmol)
3. customto react
4. filtrationA filtration
5. concentrationThe filtrate was concentrated by evaporation under vacuum
6. customa rotary evaporator
7. dissolutionThe resulting solution was dissolved with 100 mL of ethyl acetate
8. washThe resulting mixture was washed 2 times with 100 mL of NaCl(aq.)
9. customThe final product was purified by recrystallization from MeOH/H2O in the ratio 2:3
10. customThis resulted in 8.5 g (41%) of 1H-indol-3-yl acetate as a dark purple solid

ORD record

ord-e5cb03474d334acf95b8db8792e2cd23

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696229B2