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In a 1-liter flask fitted with reflux condenser with a Dry Ice trap at the condenser outlet were placed 400 ml. (445 g., 4.2 moles) of diethylene glycol and 50 g. (0.25 mole) of p-toluenesulfonic acid (with 1,56H2O —Note). The system was evacuated to 3 mm. and the mixture was refluxed to remove water. To the cooled mixture was then added 100 g. (0.35 mole) of 2-chloropropyl 3,5-dinitrobenzoate (m.p. 78.0—78.3°) [and reflux continued]. When 55 g. of liquid had been collected in the trap the material coming over was apparently largely dioxane, although it gave a positive chlorine test. Calcium chloride was added and the mixture was extracted with ether. The ether extracts were dried with calcium chloride and fractionated. The first fraction, 17.2 g., had b.p. 40—68° at 75 mm. The final fraction, 14.1 g., had b.p. 70.4—70.5° at 75 mm., n(25, D) 1.4363. The final and intermediate fractions were then refractionated, giving 13.5 g., 38% yield on the recovery from the ester and 23% yield for the over-all purification starting with the impure 2-chloropropane-1-ol. The main fraction, b.p. 70.3°/75 mm., had n(25 C, D) 1.4360, d(25/4) 1.1020.
Propene is led into an ice-cooled, rapidly stirred solution of chromyl chloride (1 mole) in CCl4 (300 ml) until the color of chromyl chloride has disappeared (absorption 23 g). The solid product that separates is hydrolysed by sodium hydrogen sulfite solution. The aqueous solution is saturated with salt and extracted with ether. The ether layer is dried over sodium sulfate and distilled. The yield of 2-chloropropan-1-ol is 43%.
© Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru