5-(chloromethyl)furan-2-carbaldehyde

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Five grams (0.028 mole) of a commercially available D-glucose was added to a three-necked flask equipped with a condenser and a stirrer, and dissolved in 5 ml of water. Thirty milli-liters of toluene was further added and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride (about 12 g) was passed through the mixture at room temperature for 30 minutes with thorough stirring. Stirring was further continued at 45° C. for 5 hours. The reaction solution containing a small amount of humud was diluted with a little water and filtered through Celite while being washed with a small amount of toluene. The toluene layer was neutralized with an aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and concentrated. Thus, about 1.0 g (theoretical yield 4.01 g) of 5-chloromethylfurfural was obtained as a crude product of pale brown color. equipped with a condenser and a stirrer Stirring The reaction solution containing a small amount of humud filtered through Celite while being washed with a small amount of toluene dried over anhydrous sodium sulfate concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Five grams (0.028 mole) of a commercially available D-glucose was added to a three-necked flask equipped with a condenser and a stirrer, and dissolved in 5 ml of water. Thirty milli-liters of toluene was further added and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride (about 12 g) was passed through the mixture at room temperature for 30 minutes with thorough stirring. Stirring was further continued at 45° C. for 5 hours. The reaction solution containing a small amount of humud was diluted with a little water and filtered through Celite while being washed with a small amount of toluene. The toluene layer was neutralized with an aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and concentrated. Thus, about 1.0 g (theoretical yield 4.01 g) of 5-chloromethylfurfural was obtained as a crude product of pale brown color. equipped with a condenser and a stirrer Stirring The reaction solution containing a small amount of humud filtered through Celite while being washed with a small amount of toluene dried over anhydrous sodium sulfate concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Five grams of a commercially available D-glucose and 97.6 mg of sodium laurylbenzenesulfonate were added to the same three-necked flask. Then, 5 ml of water and 30 ml of toluene were added thereto and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride was passed through the mixture at room temperature for about 25 minutes. Stirring was continued at 50° C. for a further 7 hours. The reaction solution was diluted with a little water and filtered through Celite while being washed with toluene. The upper toluene layer was neutralized, dried and concentrated to obtain about 1.4 g of 5-chloromethylfurfural. Stirring filtered through Celite while being washed with toluene dried concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Five grams of a commercially available D-glucose and 97.6 mg of sodium laurylbenzenesulfonate were added to the same three-necked flask. Then, 5 ml of water and 30 ml of toluene were added thereto and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride was passed through the mixture at room temperature for about 25 minutes. Stirring was continued at 50° C. for a further 7 hours. The reaction solution was diluted with a little water and filtered through Celite while being washed with toluene. The upper toluene layer was neutralized, dried and concentrated to obtain about 1.4 g of 5-chloromethylfurfural. Stirring filtered through Celite while being washed with toluene dried concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To the same three-necked flask were added 5 g of a commercially available D-glucose and two kinds of surface active agent, i.e., 97.6 mg of sodium laurylbenzenesulfonate and 89.6 mg of cetyltrimethylammonium chloride. Then, 5 ml of water and 30 ml of carbon tetrachloride were added thereto and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride was passed through the mixture at room temperature for 25 minutes. Stirring was continued at 50° C. for a further 7 hours. The reaction solution which seemed to gel slightly was filtered through Celite while being washed with small amounts of water and carbon tetrachloride. The lower carbon tetrachloride layer was neutralized, dried and concentrated to obtain about 1.5 g of 5-chloromethylfurfural. Stirring slightly was filtered through Celite while being washed with small amounts of water and carbon tetrachloride dried concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To the same three-necked flask were added 5 g of a commercially available D-glucose and two kinds of surface active agent, i.e., 97.6 mg of sodium laurylbenzenesulfonate and 89.6 mg of cetyltrimethylammonium chloride. Then, 5 ml of water and 30 ml of carbon tetrachloride were added thereto and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride was passed through the mixture at room temperature for 25 minutes. Stirring was continued at 50° C. for a further 7 hours. The reaction solution which seemed to gel slightly was filtered through Celite while being washed with small amounts of water and carbon tetrachloride. The lower carbon tetrachloride layer was neutralized, dried and concentrated to obtain about 1.5 g of 5-chloromethylfurfural. Stirring slightly was filtered through Celite while being washed with small amounts of water and carbon tetrachloride dried concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To the same three-necked flask were added 5 g of a commercially available D-glucose and two kinds of surface active agent, i.e., 97.6 mg of sodium laurylbenzenesulfonate and 89.6 mg of cetyltrimethylammonium chloride. Then, 5 ml of water and 30 ml of toluene were added thereto and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride was passed through the mixture at room temperature for 25 minutes. Stirring was continued at 50° C. for a further 7 hours. The reaction solution was diluted with a little water and filtered through Celite while being washed with toluene. The toluene layer was treated in the same manner to obtain about 1.7 g of 5-chloromethylfurfural. Stirring filtered through Celite while being washed with toluene The toluene layer was treated in the same manner

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To the same three-necked flask were added 5 g of a commercially available D-glucose and two kinds of surface active agent, i.e., 97.6 mg of sodium laurylbenzenesulfonate and 89.6 mg of cetyltrimethylammonium chloride. Then, 5 ml of water and 30 ml of toluene were added thereto and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride was passed through the mixture at room temperature for 25 minutes. Stirring was continued at 50° C. for a further 7 hours. The reaction solution was diluted with a little water and filtered through Celite while being washed with toluene. The toluene layer was treated in the same manner to obtain about 1.7 g of 5-chloromethylfurfural. Stirring filtered through Celite while being washed with toluene The toluene layer was treated in the same manner

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a three-necked flask equipped with a condenser and a stirrer were added 5 g (0.028 mole) of a commercially available D-glucose and two kinds of surface active agent, i.e., 97.6 mg (0.00028 mole) of sodium laurylbenzenesulfonate and 89.6 mg (0.00028 mole) of cetyltrimethylammonium chloride. Then, 30 ml of toluene was added thereto and the mixture was stirred to make a suspension. Thereafter, about 6 ml of 35% hydrochloric acid was slowly dropwise added from a dropping funnel over 1 hour with stirring. A slight excess of hydrogen chloride was then slowly passed therethrough at 45° C. over 3 hours with stirring. After stirring was continued for a further 4 hours, the reaction solution was diluted with a little water and filtered through Celite while being washed with toluene. The toluene layer was neutralized, dried and concentrated to obtain about 1.9 g of 5-chloromethylfurfural. To a three-necked flask equipped with a condenser and a stirrer with stirring at 45° C. over 3 hours with stirring After stirring filtered through Celite while being washed with toluene dried concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a three-necked flask equipped with a condenser and a stirrer were added 5 g (0.028 mole) of a commercially available D-glucose and two kinds of surface active agent, i.e., 97.6 mg (0.00028 mole) of sodium laurylbenzenesulfonate and 89.6 mg (0.00028 mole) of cetyltrimethylammonium chloride. Then, 30 ml of toluene was added thereto and the mixture was stirred to make a suspension. Thereafter, about 6 ml of 35% hydrochloric acid was slowly dropwise added from a dropping funnel over 1 hour with stirring. A slight excess of hydrogen chloride was then slowly passed therethrough at 45° C. over 3 hours with stirring. After stirring was continued for a further 4 hours, the reaction solution was diluted with a little water and filtered through Celite while being washed with toluene. The toluene layer was neutralized, dried and concentrated to obtain about 1.9 g of 5-chloromethylfurfural. To a three-necked flask equipped with a condenser and a stirrer with stirring at 45° C. over 3 hours with stirring After stirring filtered through Celite while being washed with toluene dried concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a three-necked flask equipped with a condenser and a stirrer were added 5 g (0.028 mole) of a commercially available D-(-)-fructose and a surface active agent, 82.3 mg (0.00028 mole) of lauryldimethylbetaine. Then, 5 ml of water and 30 ml of toluene were added thereto and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride was passed through the mixture at room temperature for about 30 minutes with thorough stirring. After the reaction was continued at room temperature for a further 3 hours, the upper toluene layer was separated from the lower aqueous layer. Thirty milli-liters of toluene and the above surface active agent in the same amount as above were then freshly added to the aqueous layer. After the reaction was carried out at room temperature for 3 hours, the upper toluene layer was again separated. This toluene extraction operation was repeated three times in total. All the toluene layers were combined and filtered through Celite. The filtrate was neutralized with an aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and concentrated. Thus, about 2.9 g of 5-chloromethylfurfural was obtained as a crude product. To a three-necked flask equipped with a condenser and a stirrer the upper toluene layer was separated from the lower aqueous layer Thirty milli-liters of toluene and the above surface active agent in the same amount as above were then freshly added to the aqueous layer After the reaction was carried out at room temperature for 3 hours the upper toluene layer was again separated This toluene extraction operation filtered through Celite dried over anhydrous sodium sulfate concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a three-necked flask equipped with a condenser and a stirrer were added 5 g (0.028 mole) of a commercially available D-(-)-fructose and a surface active agent, 82.3 mg (0.00028 mole) of lauryldimethylbetaine. Then, 5 ml of water and 30 ml of toluene were added thereto and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride was passed through the mixture at room temperature for about 30 minutes with thorough stirring. After the reaction was continued at room temperature for a further 3 hours, the upper toluene layer was separated from the lower aqueous layer. Thirty milli-liters of toluene and the above surface active agent in the same amount as above were then freshly added to the aqueous layer. After the reaction was carried out at room temperature for 3 hours, the upper toluene layer was again separated. This toluene extraction operation was repeated three times in total. All the toluene layers were combined and filtered through Celite. The filtrate was neutralized with an aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and concentrated. Thus, about 2.9 g of 5-chloromethylfurfural was obtained as a crude product. To a three-necked flask equipped with a condenser and a stirrer the upper toluene layer was separated from the lower aqueous layer Thirty milli-liters of toluene and the above surface active agent in the same amount as above were then freshly added to the aqueous layer After the reaction was carried out at room temperature for 3 hours the upper toluene layer was again separated This toluene extraction operation filtered through Celite dried over anhydrous sodium sulfate concentrated