5-(Furfurylthiomethyl)-2-Furoic Acid

  • A. L. Mndzhoian


Methyl 5-(Furfurylthiomethyl)-2-furoate. Dry benzene (150 ml) and 2.3 g (0.1 g-atom) of sodium wire were introduced into a 250-ml three-necked round-bottomed flask fitted with mercury-sealed stirrer, dropping funnel, and reflux condenser protected by a calcium chloride tube. From the dropping funnel gradual addition was made of 12.6 g (0.15 mole) of 2-furanmethanethiol (see Notes), b.p. 160°/759 mm. When the addition was complete, the mixture was boiled in a water bath and stirred gently until the sodium disappeared completely, after which the flask was cooled with water and, with continued stirring, dropwise addition was made of a solution of 17.5 g (0.1 mole) of methyl 5-(chloromethyl)-2-furoate (see Vol. 1 of this work, p. 29), b.p. 114–116°//3 mm, in 25 ml of dry benzene. The reaction mixture was boiled with stirring for three hours; it was then cooled, and 75 ml of water was added. The benzene layer was separated from the aqueous layer, which was extracted with 50 ml of ether; the ether extract was added to the benzene solution, and the whole was washed with a little water and dried over calcined sodium sulfate. Solvent was distilled off, and the residue was vacuum-distilled; 5–6 ml of head fraction came over below 175°/2 mm, and this was followed at 175–176°/2 mm by methyl 5- (furfurylthiomethyl)-2-furoate as a light-yellow oil.


Reflux Condenser Benzene Solution FURFURYL Alcohol Dropwise Addition Gradual Addition 
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Literature Cited

  1. 1.
    H. Kofod, Acta Chem. Scand. 7, 1320 (1953).Google Scholar
  2. 2.
    A. L. Mndzhoian, G. T. Tatevosian, S. G. Agbalian, and N. M. Divanian, Doklady Akad. Nauk Arm. SSR (Proc. Acad. Sci. Armenian SSR) 25, 207 (1957).Google Scholar

Copyright information

© Springer Science+Business Media New York 1959

Authors and Affiliations

  • A. L. Mndzhoian

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