In synthesis of butyrolactone derivative hydroxyester cyclisation gives no satisfactory yields. May be hydroxy-succinimide cyclize to give better yield. In that regard a direct method from ester is requested.
Ram Pratap
N-Hydroxysuccinimide is used for improved amidations in the carbodiimide method. It is also used to activate a carboxyl group and reacts with amine to form amide. It is involved in the preparation of N-hydroxymaleimide-styrene copolymer. Further, it finds use in analytical chemistry. As an additive, it is used in the carbodiimide method for improved amidations and peptide couplings. it is irritating to skin, eyes and mucous membranes
In my experience, N-Hydroxysuccinimide doesn't yield higher yields, so we need to minimize the synthesis steps and review the appropriate operating conditions. Oxidation reactions are generally uncontrollable compared to reduction reactions.
γ-Butyrolactone is produced industrially by dehydrogenation of 1,4-butanediol at a temperature of 180–300 °C and atmospheric pressure in the presence of a copper catalyst.
The yield of this process is approximately 95%. The purification takes place with a liquid-gas-phase extraction.
In the laboratory, it may also be obtained via the oxidation of tetrahydrofuran (THF), for example with aqueous sodium bromate. An alternative route proceeds from GABA via a diazonium intermediate. good luck
The Mitsunobu reaction (DEAD/Ph3P) should do the trick. Note that this will invert the stereochemistry, if any, at the alcohol position.
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