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Synthesizing 4′,4″(5″) Di‐ tert ‐butyldibenzo 18‐crown‐6 Monitored by Online FTIR
Author(s) -
Fan Juan,
Yi Chunhai,
Lan Xiaorong,
Yang Bolun
Publication year - 2014
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1815
Subject(s) - chemistry , fourier transform infrared spectroscopy , catechol , yield (engineering) , reagent , diethylene glycol , solvent , nuclear chemistry , nucleophilic substitution , nucleophile , crown ether , organic chemistry , catalysis , chemical engineering , ion , materials science , ethylene glycol , engineering , metallurgy
4′,4″(5″) Di‐ tert ‐butyldibenzo 18‐crown‐6 (DTBB18C6) was successfully synthesized by S N 2 nucleophilic substitution with 4‐ tert ‐butyl catechol as starting material. Effects of cyclization reagents, solvents, and templates were investigated. Reaction process was monitored by the real‐time online FTIR to study the actual reaction route. The highest DTBB18C6 yield (above 33%) was obtained by using Cs 2 CO 3 as the template, 2,2′‐diethylene glycol ditosylate as the cyclization reagent, and THF as the solvent. From the result of FTIR, four different reaction stages of DTBB18C6 synthesis process were proposed.