Amino acid are often esterified with methanol by using thionyl chloride or hydrogene chloride as catalist. Did you know if an important amount of methylchorid is formed ?
2006-09-26 02:07:50 · 4 answers · asked by schneiderj 2 in Science & Mathematics ➔ Chemistry
First, thionyl chloride (SOCl2) is not very commonly used. It's an older generation reagent that produces stochiometric HCl as a biproduct. Since most molecules (including many protecting groups used in amino acid chemistry) don't tolerate these harsh conditions, you are usually better off using one of the myriad of modern amino acid coupling reagents. (EDCI is a personal favorite!)
You also don't get any chloromethane with this reagent. You generally perform the reaction stepwise where you first make the acid chloride and then add the methanol. At this point there isn't any SOCl2 left, and the methanol exclusively reacts with the acid chloride.
If you really want the acid chloride, consider using CDI. It's generally very effective and typically gives higher yields since the imidazole moeity will buffer the HCl produced.
2006-09-26 12:02:55 · answer #1 · answered by rbc7snc 3 · 0⤊ 0⤋
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2016-12-15 14:32:10 · answer #2 · answered by ? 4 · 0⤊ 0⤋
think about the stability of methyl chloride and you'll have your answer
2006-09-26 03:55:32 · answer #3 · answered by shiara_blade 6 · 0⤊ 0⤋
I don't know but it sounds possible. Check with Vogel.
2006-09-26 03:23:59 · answer #4 · answered by christopher N 4 · 0⤊ 0⤋