A mixture of 22.6 g (0.12 mole) of 5-benzylfurfuryl alcohol (see p. 18), 14 g (0.14 mole) of acetic anhydride, 5 g (0.06 mole) of powdered anhydrous sodium acetate, and 80 ml of benzene was prepared in a 500-ml round-bottomed flask having side neck and fitted with mercury-sealed stirrer and reflux condenser protected by a calcium chloride tube. The stirrer was started, and the reaction mixture was boiled in a water bath for six hours. The contents of the flask were cooled and poured into a beaker containing 100 ml of cold water. The benzene layer was separated and, in order to remove the excess of acetic anhydride, it was returned to the flask and stirred with 30 ml of 5% sodium acetate solution at room temperature for two hours. The benzene layer was separated from the alkaline solution, washed with two 50-ml portions of water, and dried over anhydrous sodium sulfate. Solvent was distilled off, and the residue was vacuum-distilled: about 1 ml of head fraction was separated, and a substance coming over at 148–149°/2 mm was then collected.
KeywordsSodium Acetate Ethyl Ester Anhydrous Sodium Acetic Anhydride Heterocyclic Compound
- 1.A. L. Mndzhoian and V. G. Afrikian, Doklady Akad. Nauk Arm. SSR (Proc. Acad. Sci. Armenian SSR) 25, 201 (1957).Google Scholar