Cleavage of tert-Butyl Benzoates with NaH in DMF: Comments on the Mechanism and a Simple and Safe Alternative Procedure

Emane Filali, Guy C. Lloyd-Jones*, David A. Sale

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The hazardous and inconvenient Schmidt procedure for tert-butyl benzoate ester cleavage by NaH in DMF has been reinvestigated. The reaction is suggested to involve B(AC)2 ester cleavage, facilitated by adventitious, NaH-derived NaOH, rather than the proposed E2 elimination of isobutylene by DMF-derived NaNMe(2). Powdered KOH in THF is a significantly safer and simpler alternative that effects cleavage of tert-butyl benozoates, at ambient temperature, in excellent yield (94-99%).

Original languageEnglish
Pages (from-to)205-208
Number of pages4
Journal Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry
Issue number2
DOIs
Publication statusPublished - 22 Jan 2009

Keywords

  • tert-butyl esters
  • cleavage
  • hydrides
  • DMF
  • hazard
  • SODIUM HYDRIDE
  • ESTERS
  • HYDROLYSIS

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