Procedure:  500 mL 1-neck flask, stirbar, condenser, septum, N₂ inlet

                  Dissolved 15.362 g of I in 250 mL of absolute MeOH.  HCl gas was then bubbled through the solution for 2 min.  The reaction mixture was then refluxed for 4 h and cooled to rt.  TLC showed product spot at Rf 0.45 (1:9 EtOAc-hexanes, UV).  The solvent was removed by rotary evaporation and the material was extracted with sat. aq. NaHCO₃ and EtOAc.  The organic layer was dried over MgSO₄, filtered and the solvent removed by rotary evaporation to afford 14.970 g of product as a yellow oil which was sufficiently pure for further elaboration. 

 

¹H NMR (CDCl₃, 300 MHz) d 6.98 (m, ArH, 3H), 3.72 (s, CO₂CH₃, 3H), 3.65 (s, ArCH₂, 2H). 

 

notes

 

The acid catalyzed addition of alcohols to carboxylic acids is referred to as the Fischer esterification.  The reaction is reversible and may be driven to completion by using a large excess of alcohol or by azeotropic removal of water.