Procedure:  100 mL 1-neck flask, stirbar, septum, N₂ inlet

                  Dissolved 5.025 g of I and 2.60 mL of CH₃NO₂ in 16 mL of MeOH.  Stirred; cooled to 0 C.  Added a solution of 2.571 g of NaOH in 10 mL of water.  After 2 h, the reaction mixture was concentrated to ~10 mL and diluted with water.  The pH of the solution was lowered to 7 with concentrated HCl.  The mixture was extracted with EtOAc.  The organic layer was dried over MgSO₄, filtered and the solvent was removed by rotary evaporation to afford the product as a clear, reddish, glassy solid. 

 

¹H NMR (CDCl₃, 400 MHz) d 8.87 (d, J = 4.6 Hz, ArH, 1H), 8.21 (d, J = 8.4 Hz, ArH, 1H), 8.08 (d, J = 8.5 Hz, ArH, 1H), 7.83-7.77 (m, ArH, 2H), 7.72 (dd, J = 8.3, 1.2 Hz, ArH, 1H), 6.22 (dd, J = 9.6, 2.6 Hz, CHAr, 1H), 4.92 (dd, J = 12.9, 2.6 Hz, CH₂NO₂, 1H), 4.64 (dd, J = 12.9, 9.6 Hz, CH₂NO₂, 1H). 

 

notes

 

The Henry Reaction is an aldol type reaction with the following mechanism.