A. 1,4-Dioxaspiro[4.5]decane. A 1-l. round-bottomed flask is charged with 118 g. (1.20 moles) of cyclohexanone, 82 g. (1.32 moles) of 1,2-ethanediol, 250 ml. of reagent grade benzene, and 0.05 g. of p-toluenesulfonic acid monohydrate. The flask is attached to a water separator² under a reflux condenser fitted with a drying tube. A heating mantle is placed under the flask, and the reaction mixture is refluxed until close to the theoretical amount of water (21.6 ml.) has collected in the trap; this requires about 6 hours. The reaction mixture is cooled to room temperature, extracted successively with 200 ml. of 10% sodium hydroxide solution and five 100-ml. portions of water, dried over anhydrous potassium carbonate, and distilled through a 20-cm. Vigreux column. 1,4-Dioxaspiro[4.5]decane is obtained as a colorless liquid, b.p. 65–67° (13 mm.), weight 128–145 g. (75–85%), n²⁵D 1.4565–1.4575.

B. 2-Cyclohexyloxyethanol. A well-dried, 3-l. three-necked, round-bottomed flask is equipped with a stirrer, a pressure-equalizing dropping funnel, and a condenser to whose top is attached a calcium chloride drying tube. The flask is charged with 242 g. (1.81 moles) of anhydrous aluminum chloride powder and is immersed in an ice-salt bath. Anhydrous ether (25–50 ml.) is added dropwise through the dropping funnel, stirring is begun as soon as possible, and an additional 450–475 ml. of ether is added rapidly (total volume of ether added: 500 ml.). The mixture is stirred for approximately 30 minutes and becomes a light gray solution. During this period a mixture of 16.7 g. (0.44 mole) of lithium aluminum hydride and 500 ml. of anhydrous ether is vigorously stirred in a 1-l. round-bottomed flask under a nitrogen atmosphere (Note 1). The resulting suspension is added to the ethereal aluminum chloride solution through the dropping funnel. The resulting mixture, a gray slurry, is stirred for at least 30 minutes.

A solution of 125 g. (0.88 mole) of 1,4-dioxaspiro[4.5]decane in 200 ml. of anhydrous ether is added at a rate to cause gentle refluxing. The ice-salt bath is replaced by a steam bath, and the reaction mixture is refluxed for 3 hours. The calcium chloride drying tube is removed, and the steam bath is replaced by an ice bath. The excess hydride is carefully destroyed by adding water dropwise until hydrogen is no longer evolved; about 12 ml. of water is needed. This is followed by the more rapid addition of 1 l. of 10% sulfuric acid and then 400 ml. of water. This combination dissolves all the inorganic salts formed and results in the formation of two clear layers. The ether layer is separated in a 3-l. separatory funnel, and the aqueous layer is extracted with three 200-ml. portions of ether. The combined ethereal extracts are washed successively with 200 ml. of saturated sodium bicarbonate solution and 200 ml. of saturated brine. The ethereal solution is dried overnight over anhydrous potassium carbonate, filtered through a fluted filter paper, and concentrated by distillation on a steam bath. The residue, a pale yellow liquid weighing about 130 g., is distilled through a 20-cm. Vigreux column under reduced pressure. 2-Cyclohexyloxyethanol is obtained as a colorless liquid, b.p. 96–98° (13 mm.), weight 105–119 g. (83–94%), n²⁵D 1.4600–1.4610.