pyridine was added slowly 25.5 g. (0.25 mole) of acetic anhydride. The solution was stirred at 0" for 5 hr. and diluted with 1.0 1. of cold water. The organic layer was separated, and the aqueous layer was extracted with diethyl ether. The organic layer and ether extracts were combined and dried over anhydrous NatSOa, and the ether was removed in uacuo. The resulting yellow oil was distilled in vacuo, and the collected fraction distilled at 113-1 16"/0.2 mm. The 2-acetoxy-5methoxybenzaldehyde was collected as a white solid (TableV1).
2-Acetoxy-5-substituted Cinnamaldehydes-The procedure described for 5-substituted-2-methoxycinnamaldehydes was followed. 5Substituted-2-hydroxycinnamldehydes-To a cooled (10") solution of 2-acetoxy-5-methoxycinnamaldehyde (6.6 g., 0.03 mole) in 60 ml. of CHCh was added a solution of Na (0.69 g., 0.03 mole) in 25 ml. of CH30H. After complete addition (30 min.), the solution was stirred at 10" for 15 min. and then at room temperature for 1 hr. The reaction mixture was diluted with 100 ml. otwater, and the CHC13 layer was separated. The aqueous layer was rendered acidic by the addition of dilute H2SOn. The solid that formed was collected and washed thoroughly with water. Recrystallization from benzene gave the product as a bright-yellow solid (Table VI).