1,3-Dimethoxybenzene → 2,4,4'-Trimethoxy-alpha-methyldesoxybenzoin

Participants

Reaction Conditions

Reaction Steps

2-(p-Methoxyphenyl)propionic acid (0.39 g, 4 mmol) and 1,3-dimethoxybenzene (0.5 g, 0.5 ml, 4 mmol) were mixed in polyphosphoric acid (PPA) (10 g) and the reaction mixture was mechanically stirred at 75° C. for 5 h. The reaction mixture was then allowed to cool to room temperature and mechanically stirred for a further 12 h. The reaction was then quenched with ice water and the product extracted with CHCl3 (3×25 ml). The CHCl3 layer was dried (Na2SO4) and the solvent removed under reduced pressure. The residual crude product was purified by silica gel column chromatography (eluent 7:2 CH2Cl2:EtOAc) to give the pure 2,4,4′-trimethoxy-α-methyldesoxybenzoin (0.68 g,58%)

Provenance & Evidence