Nitration of phenol and substituted phenols with dilute nitric acid using phase-transfer catalysts

Ashutosh V. Joshi, Mubeen Baidoosi, Sudip Mukhopadhyay, Yoel Sasson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

Highly selective nitration of phenol and substituted phenols to the corresponding nitro compounds is accomplished under mild conditions in a liquid - liquid two-phase system with dilute nitric acid (6 wt %) and in the presence of a phase-transfer catalyst. The consequence of various phase-transfer catalysts on the reaction rate is contemplated. Tetrabutylammonium bromide (TBAB) was found to be the most effective phase-transfer catalyst in terms of conversion and selectivity. The experimental results are accounted for by a binary role of the phase-transfer catalyst in this system. It is anticipated to extract nitric acid into the organic phase via the hydrogen-bonded complex and to supply HBr, formed in situ in the reaction scheme by anion exchange, which is believed to be the key for generation of the active nitration species, nitronium ion in the organic phase.

Original languageEnglish
Pages (from-to)95-97
Number of pages3
JournalOrganic Process Research and Development
Volume7
Issue number1
DOIs
StatePublished - Jan 2003

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