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Cascade synthesis of dihydrobenzofuran via Claisen rearrangement of allyl aryl ethers using FeCl 3 /MCM-41 catalyst
- Source :
- Journal of Saudi Chemical Society, Vol 22, Iss 4, Pp 396-404 (2018)
- Publication Year :
- 2018
- Publisher :
- Elsevier BV, 2018.
-
Abstract
- Dihydrobenzofuran as one of the active ingredients of the naturally occurring motif is synthesized by using in situ generation of ortho allyl phenols. Aryl allyl ethers on reacting with catalytic amounts of non noble metal iron (III) chloride supported on MCM-41 under moderate reaction conditions yield dihydrobenzofuran. First step via Claisen rearrangement gives ortho allyl phenol followed by its in situ cyclization to yield dihydrobenzofuran in very good yields. Both Lewis as well as Brønsted acidity of the catalyst as evidenced by Py-FTIR studies was found to catalyze the cascade synthesis of dihydrobenzofuran. The scope of the present strategy was successfully demonstrated for several substrates with varying electronic effects for the synthesis of corresponding dihydrobenzofuran with high yields in a range of 71–86%. Keywords: Claisen rearrangement, Dihydrobenzofuran, Aryl allyl ether, MCM-41, Ferric chloride
- Subjects :
- 010405 organic chemistry
organic chemicals
Aryl
General Chemistry
010402 general chemistry
01 natural sciences
0104 chemical sciences
Catalysis
lcsh:Chemistry
Claisen rearrangement
chemistry.chemical_compound
lcsh:QD1-999
chemistry
MCM-41
Yield (chemistry)
Electronic effect
Organic chemistry
Phenol
Phenols
Subjects
Details
- ISSN :
- 13196103
- Volume :
- 22
- Database :
- OpenAIRE
- Journal :
- Journal of Saudi Chemical Society
- Accession number :
- edsair.doi.dedup.....b66230fe2b330a4273209d70e2533eeb