(2-formylphenyl) acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 30 ml of methanol were dissolved 1.74 g of 2-acetoxybenzaldehyde and 1.85 g of 2-phenoxyaniline, and after stirring at room temperature for an hour, 3.00 g of sodium borohydride was added, followed by stirring at the same temperature for 30 minutes. To the reaction solution was added dropwise an aqueous acetic acid solution (3.0 ml of acetic acid and 60 ml of water), and after stirring at room temperature for 10 minutes, the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure. A solution of the residue and 4 ml of triethylamine in 50 ml of methylene chloride was cooled to 0° C., and 2.00 ml of acetyl chloride was added dropwise with stirring, followed by stirring at room temperature for 20 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure to give a crude N-acetyl-N-(2-acetyloxybenzyl)-2-phenoxyaniline. by stirring at the same temperature for 30 minutes after stirring at room temperature for 10 minutes the mixture was extracted with ethyl acetate The extract was washed with a saturated aqueous sodium bicarbonate solution a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate After removal of the drying agent by filtration the solvent was concentrated under reduced pressure A solution of the residue and 4 ml of triethylamine in 50 ml of methylene chloride was cooled to 0° C. 2.00 ml of acetyl chloride was added dropwise with stirring by stirring at room temperature for 20 minutes The reaction mixture was poured into water extracted with ethyl acetate The extract was washed with 0.5 N hydrochloric acid a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate After removal of the drying agent by filtration the solvent was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 30 ml of methanol were dissolved 1.74 g of 2-acetoxybenzaldehyde and 1.85 g of 2-phenoxyaniline, and after stirring at room temperature for an hour, 3.00 g of sodium borohydride was added, followed by stirring at the same temperature for 30 minutes. To the reaction solution was added dropwise an aqueous acetic acid solution (3.0 ml of acetic acid and 60 ml of water), and after stirring at room temperature for 10 minutes, the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure. A solution of the residue and 4 ml of triethylamine in 50 ml of methylene chloride was cooled to 0° C., and 2.00 ml of acetyl chloride was added dropwise with stirring, followed by stirring at room temperature for 20 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure to give a crude N-acetyl-N-(2-acetyloxybenzyl)-2-phenoxyaniline. by stirring at the same temperature for 30 minutes after stirring at room temperature for 10 minutes the mixture was extracted with ethyl acetate The extract was washed with a saturated aqueous sodium bicarbonate solution a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate After removal of the drying agent by filtration the solvent was concentrated under reduced pressure A solution of the residue and 4 ml of triethylamine in 50 ml of methylene chloride was cooled to 0° C. 2.00 ml of acetyl chloride was added dropwise with stirring by stirring at room temperature for 20 minutes The reaction mixture was poured into water extracted with ethyl acetate The extract was washed with 0.5 N hydrochloric acid a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate After removal of the drying agent by filtration the solvent was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Hydroxygenzaldehyde (10 g) was dissolved in acetic anhydride (30 ml) and pyridine (30 ml) followed by stirring at room temperature for 3 hours. The reaction mixture was poured into ice-water and the resulting precipitate was recovered by filtration. The precipitate was dissolved in chloroform (100 ml), washed with water, dried and evaporated to give 2-acetoxybenzaldehyde. To a solution of 2-acetoxy-benzaldehyde (13 g) and ethyleneglycol (10 ml) in benzene (80 ml) was added Amberlist 15 (Rohm and Haas Co.) (3 g) and followed by refluxing for 5 hours. Water generated during refluxing was removed as an azeotropic mixture. The reaction mixture was washed with an aqueous solution of sodium bicarbonate, and then with water, and dried and evaporated. The residue was distilled under reduced pressure to collect a fraction distilled out at 115°-125° C./4 mmHg to give 10 g of 2-(2-acetoxyphenyl)-1,3-dioxolan. To a solution of 2-(2-acetoxy-phenyl)-1,3-dioxolan (19.6 g) in dichloromethane (50 ml), bis(trimethylsilyl)-5-fluorouracil prepared as in Example 1 from 5-fluorouracil (10 g) was added and treated as in Example 10 to give 4.2 g of crystalline 1-[α-(2-hydroxyethoxy)-2-acetoxybenzyl]-5-fluorouracil. by refluxing for 5 hours during refluxing was removed as an azeotropic mixture The reaction mixture was washed with an aqueous solution of sodium bicarbonate with water, and dried evaporated The residue was distilled under reduced pressure to collect a fraction distilled out at 115°-125° C./4 mmHg

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 30 ml of methanol were dissolved 1.74 g of 2-acetoxybenzaldehyde and 1.85 g of 2-phenoxyaniline, and after stirring at room temperature for an hour, 3.00 g of sodium borohydride was added, followed by stirring at the same temperature for 30 minutes. To the reaction solution was added dropwise an aqueous acetic acid solution (3.0 ml of acetic acid and 60 ml of water), and after stirring at room temperature for 10 minutes, the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure. A solution of the residue and 4 ml of triethylamine in 50 ml of methylene chloride was cooled to 0° C., and 2.00 ml of acetyl chloride was added dropwise with stirring, followed by stirring at room temperature for 20 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure to give a crude N-acetyl-N-(2-acetyloxybenzyl)-2-phenoxyaniline. by stirring at the same temperature for 30 minutes after stirring at room temperature for 10 minutes the mixture was extracted with ethyl acetate The extract was washed with a saturated aqueous sodium bicarbonate solution a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate After removal of the drying agent by filtration the solvent was concentrated under reduced pressure A solution of the residue and 4 ml of triethylamine in 50 ml of methylene chloride was cooled to 0° C. 2.00 ml of acetyl chloride was added dropwise with stirring by stirring at room temperature for 20 minutes The reaction mixture was poured into water extracted with ethyl acetate The extract was washed with 0.5 N hydrochloric acid a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate After removal of the drying agent by filtration the solvent was concentrated under reduced pressure