[93-97-0] · C14H10O3 · Benzoic Anhydride · (MW 226.23)
Physical Data: mp 42-43 °C; bp 360 °C; d 1.199 g cm-3.
Solubility: insol H2O; sol alcohol, ether, CHCl3, acetone, EtOAc, benzene, toluene, glacial acetic acid, acetic anhydride; slightly sol pet ether.
Form Supplied in: white crystalline solid; widely available.
Purification: benzoic acid is removed by washing with NaHCO3, then water, followed by drying. The reagent can be recrystallized from benzene (0.5 mL g-1) by adding a small amount of pet ether (bp 40-60 °C) and cooling. It can also be distilled at 210-220 °C at 20 mmHg.
Handling, Storage, and Precautions: irritating to eyes, respiratory system, and skin. May decompose on exposure to moist air or water.
The most common use of this reagent is as a protecting group for oxygen1a,b and nitrogen1c functional groups. The ease of benzoylation and the ready removal of the protecting group under mildly basic conditions render it valuable in organic synthesis.1a In addition, this reagent has found many uses as an acylating agent for stabilized carbanions.1d,e Its participation in the Friedel-Crafts acylation reaction1f is well known and has been extended to processes involving Lewis acid catalysts.1g In the presence of Titanium(IV) Chloride and Silver(I) Perchlorate as catalysts, this reagent reacts with silyl derivatives of acids and alcohols to give Addition of an excess of this reagent to alkynes, promoted by a This reagent has been shown to Kevin Daniels The Ohio State University, Columbus, OH, USA
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Addition of an excess of this reagent to alkynes, promoted by a This reagent has been shown to Kevin Daniels The Ohio State University, Columbus, OH, USA
This reagent has been shown to
The Ohio State University, Columbus, OH, USA