Ghost_Of_BT (Hive Bee)
09-22-01 12:36
No 216209
       How to make IAA methyl/ethyl ester  Bookmark   

A while back, I saw a page giving some general proceedures for making methyl and ethyl esters, but I can't find it again (dont you hate when that happens). Could someone please give the proceedure for making IAA methyl or ethyl ester? 		 
 
 
 
    Ghost_Of_BT
(Hive Bee)
09-24-01 13:36
No 216748
       Re: How to make IAA methyl/ethyl ester  Bookmark   

I took some notes from a couple textbooks on esterification:

-Esterificatiton reactions proceed very slowly without an acid catalyst but reach equalibrium in only a few hours when an alcohol and acid are refluxed with a small amount of concentrated H2SO4 or HCl.
-HCl is passed through a mixture of alcohol and acid untill solution gains 3% weight and it is than refluxed (Fisher-Sperier method). Yeilds very good.
-The caboxylic esters are sweet smeling solids or liquids.

I guesse I answered my own question. My plan is to reflux a solution of IAA and 3% HCl for a few hours and evaporate. Any apperent problems with that? 		 
 
 
 
    Rhodium
(Chief Bee)
09-24-01 14:16
No 216756
       Re: How to make IAA methyl/ethyl ester  Bookmark   

In that case, make that 3% HCl in anhydrous methanol/ethanol. Water pushes the equilibrium the wrong way. 		 
 
 
 
    Ghost_Of_BT
(Hive Bee)
09-24-01 17:37
No 216849
       Re: How to make IAA methyl/ethyl ester  Bookmark   

Oops, that was a typo. I meant to say 3% HCl in methanol. Thanks.