Titlebook: Synthesis of Heterocyclic Compounds; A. L. Mndzhoian Book 1959 Springer-Verlag US 1959 Alkaloid.alkaloids.biology.chemistry.cyclic compoun

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2-Methylfuran (Sylvan),e of the U-tube was connected to a sloping condenser, which was fitted with a long receiver adapter; the end of the adapter was in the lower part of a long-necked 100-ml flask, which served as a receiver and was cooled with ice water.

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Furan,ed with pieces of sodium hydroxide of the size of a pea, which are separated from the end of the tube E by a layer of cotton wool (Note 1). The column F is immersed in a water bath (a tall beaker) at 45–50°. The exit tube of the column F is connected to a sloping condenser attached to a receiver immersed in ice and salt (Note 2).

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5-Benzyl-2-Furoic Acid,A mixture of 21.6 g (0.1 mole) of methyl 5-benzyl-2-furoate (see p. 17), b.p. 150–155° /1 mm, and 50 ml of 10% sodium hydroxide solution was prepared in a 150-ml round-bottomed flask fitted with stirrer and reflux condenser.

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Methyl 2-Furoate,A. A solution of 224 g (2 moles) of 2-furoic acid . p. 43), m.p. 128–132°, in 500 ml of methanol was placed in a one-liter flask fitted with a reflux condenser and a glass tube, which passed to the bottom of the flask.

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5-Methyl-2-Furoic Acid,A mixture of 14 g (0.1 mole) of methyl 5-methyl-2-furoate (see p. 23), b.p. 97–99°/12 mm, and 22 ml of 22% aqueous sodium hydroxide solution was prepared in a 100-m1 round-bottomed flask fitted with mercury-sealed stirrer and reflux condenser.

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5-(Propoxymethyl)-2-Furoic Acid,Ground sodium hydroxide (35 g) was added with stirring to 96% alcohol (130 ml) contained in a 500-ml three-necked round-bottomed flask fitted with mercury-sealed stirrer, reflux condenser, and dropping funnel. With continued stirring, 61 g (0.3 mole) of methyl 5-(propoxymethyl)-2-furoate (see p. 25), b.p. 146–148°//12 mm, was added gradually.

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