- Synthesis of 3-Phenyl-1-propanol
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3-Phenyl- (CAS no.: ), which is also known as 1-Propanol, 3-phenyl-, could be produced through the following synthetic route.
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In a 5-l. round-bottomed flask, equipped with two reflux condensers and a mechanical stirrer, are placed 800 g. (925 ml.) of dry toluene and 168 g. (7.3 g. atoms) of sodium. The toluene is heated to boiling, the sodium is melted, and the stirrer is started. The source of external heat is removed, and a solution of 328 g. (2 moles) of 4-phenyl-m-dioxane (p. 786) in 311 g. (4.2 moles) of 1-butanol is added through the top of one of the condensers. The vapors should reflux about halfway up the condensers; about 30 to 60 minutes is used for the addition. The mixture is cooled to room temperature, and a solution of 100 ml. of concentrated sulfuric acid in 800 ml. of water is added slowly with stirring. After the water layer is separated and discarded, 500 ml. of water is again added to the organic layer. Dilute sulfuric acid (5%) is added with shaking until the water layer is neutral to litmus paper. After the water layer is separated and discarded, the toluene and 1-butanol are removed from the organic layer by distillation. The remaining liquid is fractionated under reduced pressure to give 224–227 g. (82.2–83.4%) of 3-phenyl-1-propanol, b.p. 95–97°/0.4 mm. or 113–115°/3 mm., nD20 1.5268–1.5269, d420 1.004–1.008.
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