phosphoric acid,2-naphthalenyl diphenyl ester

General procedure: To a solution of alcohol component (0.9 mmol), pyridine-N-oxide (0.045 mmol, 5 molpercent) andProton Sponge© (1.8 mmol) in CH2Cl2 (0.2 M) was added the specified phosphoryl chloride(1.0 mmol). The reaction mixture was stirred at room temperature for the time specifiedbefore the addition of MeOH (2 mL). The reaction mixture was then conc. in vacuo and crudematerial purified by flash chromatography to afford the desired productGeneral procedure: To a solution of alcohol component (0.9 mmol), pyridine-N-oxide (0.045 mmol, 5 mol%) andProton Sponge (1.8 mmol) in CH2Cl2 (0.2 M) was added the specified phosphoryl chloride(1.0 mmol). The reaction mixture was stirred at room temperature for the time specifiedbefore the addition of MeOH (2 mL). The reaction mixture was then conc. in vacuo and crudematerial purified by flash chromatography to afford the desired productInto a one-liter four-necked flask provided with a stirrer, a condenser and a thermometer, 144.2 g (1 mole) of 2-naphthol, 199.4 g (1.3 moles) of phosphorus oxychloride and 0.5 g of anhydrous magnesinum chloride were fed. Then, the resulting mixed solution was heated with stirring in nitrogen atmosphere to 120 C in an hour, and then reacted by stirring at the same temperature (120 C) for an hour. After the reaction, the pressure was reduced to about 1.5 kPa while maintaining the solution at 120 C to recover excess (unreacted) phosphorus oxychloride. Subsequently, the reaction mixture was cooled to room temperature, and then 188.0 g (2 moles) of phenol (equivalent to 1.14 moles with respect to one mole of chlorine existing in the reaction product) and 10 g of toluene were added. The resulting mixed solution was heated with stirring in nitrogen atmosphere to 160 C in 2 hours, and then reacted for 3 hours while refluxing toluene under a reduced pressure (about 20 kPa) at the same temperature (160 C). The reaction solution was cooled to 80 C, nitrogen was introduced into the flask to set the pressure inside the flask to an atmospheric pressure, and the reaction solution was washed with a 3.5 % aqueous solution of hydrochloric acid and a 1 % aqueous solution of sodium hydroxide successively and finally with water at the same temperature (80 C). Further, the resulting solution was steam distilled under a reduced pressure (about 2.7 kPa) at 150 C to remove low boiling point components from the reaction product, thereby obtaining 344 g of a pale brownish solid. Assuming that the solid as a whole was the target compound, the rough yield of the product was 91 %. Comparative Example 1. A pale brownish sticky solid of 341 g was obtained in the same manner as in except that 168.7 g (1.1 moles) of phosphorus oxychloride was used. Assuming that the solid as a whole was the target compound, the rough yield of the product was 91 %. The phenol of 2 moles used in the Step (2) was equivalent to 1.15 moles with respect to one mole of chlorine existing in the reaction product.Comparative Example 3. A pale brownish liquid of 457 g was obtained in the same manner as in except that unreacted phosphorus oxychloride was not recovered and that 272.9 g (2.9 moles) of phenol (equivalent to 1 mole with respect to one mole of chlorine existing in the reaction product) was used. The rough yield of the product was 96 %, assuming that the liquid was a mixture of 0.3 moles of triphenyl phosphate and 1 mole of naphthyl diphenyl phosphate.A pale brownish solid of 346 g was obtained in the same manner as in except that 0.5 g of anhydrous aluminum chloride was used in place of 0.5 g of anhydrous magnesium chloride. Assuming that the solid as a whole was the target compound, the rough yield of the product was 92 %. The phenol of 2 moles used in the Step (2) was equivalent to 1.11 moles with respect to one mole of chlorine existing in the reaction product in Step (1).Into a two-liter four-necked flask provided with a stirrer, a condenser and a thermometer, 289.0 g (2 moles) of 2-naphthol, 307.0 g (2 moles) of phosphorus oxychloride and 3.0 g of anhydrous aluminum chloride were fed. Then, the mixed solution was heated with stirring in a nitrogen atmosphere to 150 C in 5 hours. Then, the resulting mixture was further heated to 165 C in 3 hours to be reacted. Subsequently, the reaction solution was cooled to room temperature, and then 376.0 g (4 moles) of phenol was added. The resulting mixed solution was heated with stirring in a nitrogen atmosphere to 190 C in 6 hours, and then reacted by heating to 200 C in 3 hours. The reaction solution was cooled and dissolved in the substantially same volume of carbon tetrachloride, and the resulting solution was washed with shaking with a 3 % aqueous solution of sodium chloride three times and finally with water. Then, the carbon tetrachloride was distilled off under reduced pressure, and the solution was further distilled under a reduced pressure (about 70 kPa) to remove distillate whose boiling point is up to 180 C, thereby obtaining 719 g of a pale brownish liquid. Assuming that the solid as a whole was the target compound, the rough yield of the product was 96 %.A pale brownish solid of 360 g was obtained in the same manner as in except that 306.7 g (2.0 moles) of phosphorus oxychloride was used. Assuming that the solid as a whole was the target compound, the rough yield of the product was 96 %. The phenol of 2 moles used in the Step (2) was equivalent to 1.06 moles with respect to one mole of chlorine existing in the reaction product in Step (1).Example 3. A pale brownish solid of 361 g was obtained in the same manner as in except that 460.1 g (3.0 moles) of phosphorus oxychloride was used. Assuming that the solid as a whole was the target compound, the rough yield of the product was 96 %. The phenol of 2 moles used in the Step (2) was equivalent to 1.04 moles with respect to one mole of chlorine existing in the reaction product in Step (1). The composition and melting point of the obtained product were determined in the same manner as in Example 1. The results are shown in Table 1 together with the metallic halide and the molar ratio of phosphorus oxychloride to naphthol used.

Molecular Weight:376.3
XLogP3:6.5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:376.08644602
Monoisotopic Mass:376.08644602
Topological Polar Surface Area:44.8
Heavy Atom Count:27
Complexity:475
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes