Methyl 5-Benzyl-2-furoate. A solution of 40.4 g (0.2 mole) of 5-benzyl-2-furoic acid (see Vol. 1 of this work, p. 7), m.p. 104–105°, in 200 ml of anhydrous methanol was introduced into a 500-ml three-necked round-bottomed flask fitted with mercury-sealed stirrer, reflux condenser, and glass tube passing to the bottom of the flask. The stirred solution was heated in a water bath to a steady boil, which was maintained for 2.5–3 hours while a rapid stream of hydrogen chloride was passed (the hydrogen chloride was first passed through a wash bottle containing concentrated sulfuric acid). The solution was cooled and poured into a flask containing 500 ml of cold water; the oily product was separated, and the aqueous layer was extracted with three 75-ml portions of ether. The ethereal extract was added to the main product, and the whole was washed with 5% sodium carbonate solution and with water; it was dried over calcined sodium sulfate. Ether was distilled off, and the residue was vacuum-distilled and came over at 160–162°/3 mm. Yield 38.4–39.8 g (88.8–89.3%).
KeywordsAluminum Chloride Reflux Condenser Ethereal Solution Sodium Carbonate Solution Hydrogen Chloride
Unable to display preview. Download preview PDF.