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.
KeywordsReflux Condenser Benzene Solution FURFURYL Alcohol Dropwise Addition Gradual Addition
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