1123890-53-8Relevant articles and documents
Cleavage of tert-butyl benzoates with NaH in DMF: Comments on the mechanism and a simple and safe alternative procedure
Filali, Emane,Lloyd-Jones, Guy C.,Sale, David A.
, p. 205 - 208 (2009)
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 BAC2 ester cleavage, facilitated by adventitious, NaH-derived NaOH, rather than the proposed E2 elimination of isobutylene by DMF-derived NaNMe2. 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%). Georg Thieme Verlag Stuttgart.