Esterification with thionyl chloride and methanol mechanism
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I have two methods of going about this reaction. The first one was suggested by a chemist in another lab:
1. Add 1:3 equivalence ratio of 5-aminonicotinic acid to thionyl chloride (SOCl2) in an excess of methanol (to form methyl ester). First, add SOCl2 dropwise to chilled 5-aminonicotinic acid in methanol in an ice water bath with drying tube (anhydrous). Allow reaction to stir for 30 minutes on ice and then gradually bring up to room temperature. Then, reflux overnight for about 16 hours under anhydrous conditions. Rotovap away methanol and then dissolve remaining in water and 1 N NaOH (about 50 mL) and verify the pH to be between 7-8. Next, extract with 3x 50 mL ethyl acetate. Wash EtOAc with brine, dry with sodium sulfate, filter, and then concentrate again to obtain final product.
1. Add 1:3 equivalence ratio of 5-aminonicotinic acid to thionyl chloride (SOCl2) in an excess of methanol (to form methyl ester). First, add SOCl2 dropwise to chilled 5-aminonicotinic acid in methanol in an ice water bath with drying tube (anhydrous). Allow reaction to stir for 30 minutes on ice and then gradually bring up to room temperature. Then, reflux overnight for about 16 hours under anhydrous conditions. Rotovap away methanol and then dissolve remaining in water and 1 N NaOH (about 50 mL) and verify the pH to be between 7-8. Next, extract with 3x 50 mL ethyl acetate. Wash EtOAc with brine, dry with sodium sulfate, filter, and then concentrate again to obtain final product.
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