Phenyl Acetate Preparation M. B. Hocking1 McGill University Montreal, Quebec H3A 2A7
from Phenol and Acetic Acid Reassessment of a common
It is often stated (or implied) by authors of textbooks in organic chemistry that ”... phenols cannot be esterified directly” (f). Discussion of direct esterification is often dismissed in this way (2) and methods using acid derivatives are outlined, even in the periodical literature (3). This paper reports the determination of the approximate equilibrium concentrations for the phenol and acetic acid system, together with an effective method for the direct preparation of phenyl acetate using a combination of mass action and azeotropic one pass water removal to drive this equilibrium to the right to obtain workable ester yields. Experimental
J. Chem. Educ. 1980.57:527. Downloaded from pubs.acs.org by IOWA STATE UNIV on 01/07/19. For personal use only.
Equilibration rates and equilibria Three experiments were run, each using 18.8 g phenol (0.20 mol) and 12.0 g glacial acetic acid (0.20 mol) in flasks fitted with reflux condensers. All three were boiled under reflux, one without catalyst, and the second and third with 23 mg and 250 mg of cone, sulfuric acid, respectively. After 22 hr boiling, the first had no phenyl acetate (
