1-苯氧基乙醇

反应条件: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Phenoxyethanol (440 g, 3.1874 mol) was dissolved in 880 ml of a mixed solution of acetic acid/water =7/3. Sodium acetate (340 g, 4.1436 mol) was added and cooled to 15° C. A solution resulting from dissolving bromine (514.5 g, 3.22 mol) in 1760 ml of a mixed solution of acetic acid/water=7/3 was dropped while keeping at 15-20° C. and then was stirred at 10-20° C. for 30 minutes. Yellow color remained a little. Six milliliter of a 10 W/W% aqueous sodium sulfite solutions was dropped. The mixture became colorless. Dropping 2200 ml of water caused clouding. Crystallization was conducted by addition of seed crystals and stirring at room temperature for 30 minutes. After adding 4400 ml of water, stirring was done at room temperature for 30 minutes and at 0-10° C. for 1.5 hours. The crystals were filtered and washed with 3 L of water. After overnight air-drying and vacuum drying (35-40° C.) for 16 hours, 631 g (Yield 91.3%) of p-bromophenoxyethanol was obtained as white crystals. A solution resulting was dropped while keeping at 15-20° C. Crystallization was conducted by addition of seed crystals stirring at room temperature for 30 minutes After adding 4400 ml of water stirring was done at room temperature for 30 minutes and at 0-10° C. for 1.5 hours The crystals were filtered washed with 3 L of water After overnight air-drying vacuum drying (35-40° C.) for 16 hours

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1 mol of phenoxyethanol is esterified azeotropically in the presence of 1.1 mol of H3PO3 in xylene on a water separator. The reaction product which precipitates on cooling is filtered off, washed with petroleum ether and dried to give a white powder. The amount of the phosphoric diester (2-phenoxyethanol hydrogensulphate, 0-50%) which may be formed in this reaction in addition to phenoxyethanol phosphate (phenoxyethanol dihydrogenphosphate) does not interfere in the polycondensation which subsequently takes place; it is also incorporated into the polycondensate. The reaction product which precipitates on cooling is filtered off washed with petroleum ether dried to give a white powder

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1 mol of phenoxyethanol is esterified azeotropically in the presence of 1.1 mol of H3PO3 in xylene on a water separator. The reaction product which precipitates on cooling is filtered off, washed with petroleum ether and dried to give a white powder. The amount of the phosphoric diester (2-phenoxyethanol hydrogensulphate, 0-50%) which may be formed in this reaction in addition to phenoxyethanol phosphate (phenoxyethanol dihydrogenphosphate) does not interfere in the polycondensation which subsequently takes place; it is also incorporated into the polycondensate. The reaction product which precipitates on cooling is filtered off washed with petroleum ether dried to give a white powder

反应条件: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Phenoxyethanol (440 g, 3.1874 mol) was dissolved in 880 ml of a mixed solution of acetic acid/water =7/3. Sodium acetate (340 g, 4.1436 mol) was added and cooled to 15° C. A solution resulting from dissolving bromine (514.5 g, 3.22 mol) in 1760 ml of a mixed solution of acetic acid/water=7/3 was dropped while keeping at 15-20° C. and then was stirred at 10-20° C. for 30 minutes. Yellow color remained a little. Six milliliter of a 10 W/W% aqueous sodium sulfite solutions was dropped. The mixture became colorless. Dropping 2200 ml of water caused clouding. Crystallization was conducted by addition of seed crystals and stirring at room temperature for 30 minutes. After adding 4400 ml of water, stirring was done at room temperature for 30 minutes and at 0-10° C. for 1.5 hours. The crystals were filtered and washed with 3 L of water. After overnight air-drying and vacuum drying (35-40° C.) for 16 hours, 631 g (Yield 91.3%) of p-bromophenoxyethanol was obtained as white crystals. A solution resulting was dropped while keeping at 15-20° C. Crystallization was conducted by addition of seed crystals stirring at room temperature for 30 minutes After adding 4400 ml of water stirring was done at room temperature for 30 minutes and at 0-10° C. for 1.5 hours The crystals were filtered washed with 3 L of water After overnight air-drying vacuum drying (35-40° C.) for 16 hours

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Further, the inventors of the present invention disclose, as a method using no sulfuric acid, a method of obtaining 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene by reacting fluorenone with phenoxyethanol in the presence of a heteropoly acid serving as a catalyst, which method includes (a) partitioning a target substance into an organic phase by adding an extract agent constituted by water and an organic solvent to a reaction liquid and (b) recovering the target substance (refer to Patent Literature 8). Further, the inventors of the present invention propose: a method for producing 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene from fluorenone and 2-phenoxyethanol in the presence of a heteropoly acid catalyst (Patent Literature 9); and a method for producing 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene whose melting point is 160° C. to 166° C. (Patent Literature 10). Moreover, there is disclosed a method of obtaining a fluorene derivative by reacting fluorenone with a phenol by using hydrochloric acid and a thiol serving as catalysts, which method includes partitioning a target substance into an organic phase by using an extract agent and recovering the target substance (refer to Patent Literature 11). However, according to these methods, a reaction liquid contains a large amount of unreacted phenol or phenoxyalcohol, which is highly soluble in water. This may cause a reduction in liquid separability, and thus cause a deterioration in hue or purity. Further, these methods place a large burden on the environment, because a large amount of organic compounds such as phenols or phenoxyalcohols are mixed in an aqueous phase, and/or it is necessary to use a large amount of organic solvent for liquid separation. Therefore, these methods are not industrially advantageous. partitioning a target substance into an organic phase by adding an extract agent an organic solvent to a reaction liquid and (b) recovering the target substance (refer to Patent Literature 8)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 50% of 20% strength carbendasulf solution from Example 9 was combined with 10% of Proxel press paste (BIT) and 40% of phenoxyethanol and stirred for about 1 hour, giving a clear deep red solution. giving a clear deep red solution

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 50% of 20% strength carbendasulf solution from Example 9 was combined with 10% of Proxel press paste (BIT) and 40% of phenoxyethanol and stirred for about 1 hour, giving a clear deep red solution. giving a clear deep red solution

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 50% of 20% strength carbendasulf solution from Example 9 was combined with 10% of Proxel press paste (BIT) and 40% of phenoxyethanol and stirred for about 1 hour, giving a clear deep red solution. giving a clear deep red solution

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Synthesis of N-[1-(2-phenoxyethan-1-yl)piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide Under nitrogen gas, 0.37 ml (4.78 mM) of methanesulfonyl chloride was added to a solution of 0.44 g (3.18 mM) of phenoxyethanol and 0.89 ml (6.39 mM) of triethylamine in methylene chloride (6 ml) at 0° C. and the mixture was stirred at the prevailing temperature for 35 minutes. The reaction was stopped by adding saturated aqueous solution of sodium hydrogen carbonate and the reaction mixture was extracted with diethyl ether. The organic layer was washed serially with water and saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide 0.6989 g (<3.18 mM) of phenoxyethyl mesylate. To a solution of 0.58 g (1.5 mM) of N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride and 1.0 ml (7.2 mM) of triethylamine in ethanol (6.0 ml) was added 0.6989 g (<3.18 mM) of the above phenoxyethyl mesylate at room temperature and the mixture was refluxed under nitrogen for 17 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The resulting crude product was purified by column chromatography (methanol/ethyl acetate 30-40%) to provide the title compound. the reaction mixture was extracted with diethyl ether The organic layer was washed serially with water and saturated aqueous solution of sodium chloride dried over MgSO4 The solvent was then distilled off under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 50% of 20% strength carbendasulf solution from Example 9 was combined with 10% of Proxel press paste (BIT) and 40% of phenoxyethanol and stirred for about 1 hour, giving a clear deep red solution. giving a clear deep red solution

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The hyperbranched chromophore II (5.0 g, corresponding to 5% (w/w) UV-filter/sunscreen) was dissolved in Tegosoft TN at 80° C. and added to a mixture of Brij 72 (INCI: Steareth-2) (2.0 g), Brij 721 (INCI: Steareth-21) (2.0 g), Lanette O (cetearyl alcohol) (2.0 g), Estol GMM 3650 (glyceryl monomyristate) (2.0 g), BHT (butylhydroxytoluene) (0.05 g) and Phenonip (phenoxyethanol and methyl-, ethyl-, propyl-, butylparaben) (0.8 g). The mixture was shortly heated to 80° C. in order to melt solid emulsifiers. To the still warm mixture (70-80° C.) a preheated solution (˜80° C.) of glycerin (4.0 g) and EDTA BD (0.1 g) in water (62.95 g) and subsequently 10% aqueous KOH (0.1 g) as well as Sepigel 305 (polyacrylamide and C13-C14 isoparaffin and Laureth-7) (1.0 g) were added slowly under continuous stirring. The resulting emulsion was stirred until a temperature of about 40° C. was reached, homogenized with 24,000 rpm using a ULTRA-TURRAX®, and finally stirred for an additional hour. Determination of the photostability of the novel polymeric chromophore II was performed according to G. Berset et al. (International Journal of Cosmetic Science 1996, 18(3), 167-177) applying instead of a liquid film the prepared sunscreen. Thereby 96% of the chromophore II could have been recovered. In vitro SPF measurements were performed in comparison to a sunscreen containing 5% Parsol® MCX (2-ethylhexyl 4-methoxycinnamate) after application of 1.4 mg sunscreen per cm2 on PMMA plates (Helioscience, Marseille, FR) using the SPF-290S Analyzer System (Optometrics LLC, Chicago, US). Each in vitro SPF was determined in triplicate to give for chromophore II and Parsol® MCX an average of 6.6 (II) and 6.8, respectively. homogenized with 24,000 rpm finally stirred for an additional hour Thereby 96% of the chromophore II could have been recovered containing 5% Parsol® MCX (2-ethylhexyl 4-methoxycinnamate) after application of 1.4 mg

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1 mol of phenoxyethanol is esterified azeotropically in the presence of 1.1 mol of H3PO3 in xylene on a water separator. The reaction product which precipitates on cooling is filtered off, washed with petroleum ether and dried to give a white powder. The amount of the phosphoric diester (2-phenoxyethanol hydrogensulphate, 0-50%) which may be formed in this reaction in addition to phenoxyethanol phosphate (phenoxyethanol dihydrogenphosphate) does not interfere in the polycondensation which subsequently takes place; it is also incorporated into the polycondensate. The reaction product which precipitates on cooling is filtered off washed with petroleum ether dried to give a white powder