Indole 3 acetic acid -> methyl indole acetate
I'm trying to convert indole acetic acid to its methyl ester, I tried the fischer-speier esterification via 5g indole acetic acid in 300mL methanol
with 10 drops 98% conc. sulfuric acid. Refluxed for 2.5 hrs. At which point tlc showed absence of IAA. Solution started light pink, went to amber.
Upon completions neutralized with a small amount of CaCO3. Solution exploded like a baking soda/vinegar volcano from grade school... Solution went
from dark urine to amber creme with addition of CaCO3. Once settled I Vacuum filtered solids, leaving the solution slightly reddish color. tried to
vacuum distill liquid but aparently my aspirator isnt strong enough. so i boiled 80% of the liquid off. Let the rest evaporate at room temp over night
and left with dark blood red oil. Methyl ester should be a beige colored crystal....
Anyone have experience with this? Would more acid catalyst be necessary or perhaps ended up with an intermediate? What might have gone wrong to end up
with an oil?
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