4-(2-FURYL)-1-BUTEN-4-OL 97

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 350 ml of a water-acetone (1:6 by volume) mixture, was dissolved 10 g of 2-(1-hydroxy-3-butenyl)-furan. To the solution heated at 55° C. under reflux, was added dropwise 6.6 g of polyphosphoric acid. After having been stirred at 55° C. for 48 hours, the reaction mixture was stripped of the acetone by distillation and the residue was extracted twice with 300 ml of ether. The extract solution was washed with an aqueous sodium hydrogencarbonate solution, then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and freed from the solvent by distillation to obtain 9.5 g of a concentrate. On distillation of the concentrate, there were obtained 4.2 g of 2-(1-hydroxy-3-butenyl)furan (b.p. 78° C./10 mmHg) and 3.8 g (65.5% yield based on consumed starting material) of the intended 4-hydroxy-5-allyl-2-cyclopentenone (b.p. 97° C./0.7 mmHg). under reflux the reaction mixture was stripped of the acetone by distillation the residue was extracted twice with 300 ml of ether The extract solution was washed with an aqueous sodium hydrogencarbonate solution with saturated sodium chloride solution, dried over anhydrous sodium sulfate freed from the solvent by distillation to obtain 9.5 g of a concentrate On distillation of the concentrate

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 350 ml of a water-acetone (1:6 by volume) mixture, was dissolved 10 g of 2-(1-hydroxy-3-butenyl)furan. To the solution heated at 55° C. under reflux, was added dropwise 6.6 g of polyphosphoric acid. After having been stirred at 55° C. for 96 hours, the reaction mixture was freed from the acetone by distillation and the residue was extracted twice with 300 ml of ether. The extract solution was washed with an aqueous sodium hydrogencarbonate solution, then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and freed from the solvent by distillation to obtain 8.5 g of a concentrate. The concentrate was purified by a column chromatography using 100 g of a silica gel (Wako Gel C-200) and a toluene-ether (2:1 by volume) mixture as eluent, to obtain 4.3 g (43% yield) of 4-hydroxy-5-allyl-2-cyclopentenone. under reflux the reaction mixture was freed from the acetone by distillation the residue was extracted twice with 300 ml of ether The extract solution was washed with an aqueous sodium hydrogencarbonate solution with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate freed from the solvent by distillation to obtain 8.5 g of a concentrate The concentrate was purified by a column chromatography

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

Procedure: Reaction and after-treatment were carried out in the same manner as in Example 3 except that an equimolar amount of furfural was used in place of 5-methylfurfural, and that ammonium bromide and tetrahydrofuran were used in place of ammonium chloride and toluene, respectively, in the same weights as those of the latter, to obtain 50.6 g of the fraction of 2-(1-hydroxy-3-butenyl)-furan (content, 99.3%) (yield, 91.0%). Reaction

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

Procedure: Reaction and after-treatment were carried out in the same manner as in Example 3 except that an equimolar amount of furfural was used in place of 5-methylfurfural, and that ammonium bromide and tetrahydrofuran were used in place of ammonium chloride and toluene, respectively, in the same weights as those of the latter, to obtain 50.6 g of the fraction of 2-(1-hydroxy-3-butenyl)-furan (content, 99.3%) (yield, 91.0%). Reaction

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 350 ml of a water-acetone (1:6 by volume) mixture, was dissolved 10 g of 2-(1-hydroxy-3-butenyl)-furan. To the solution heated at 55° C. under reflux, was added dropwise 6.6 g of polyphosphoric acid. After having been stirred at 55° C. for 48 hours, the reaction mixture was stripped of the acetone by distillation and the residue was extracted twice with 300 ml of ether. The extract solution was washed with an aqueous sodium hydrogencarbonate solution, then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and freed from the solvent by distillation to obtain 9.5 g of a concentrate. On distillation of the concentrate, there were obtained 4.2 g of 2-(1-hydroxy-3-butenyl)furan (b.p. 78° C./10 mmHg) and 3.8 g (65.5% yield based on consumed starting material) of the intended 4-hydroxy-5-allyl-2-cyclopentenone (b.p. 97° C./0.7 mmHg). under reflux the reaction mixture was stripped of the acetone by distillation the residue was extracted twice with 300 ml of ether The extract solution was washed with an aqueous sodium hydrogencarbonate solution with saturated sodium chloride solution, dried over anhydrous sodium sulfate freed from the solvent by distillation to obtain 9.5 g of a concentrate On distillation of the concentrate

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 350 ml of a water-acetone (1:6 by volume) mixture, was dissolved 10 g of 2-(1-hydroxy-3-butenyl)-furan. To the solution heated at 55° C. under reflux, was added dropwise 6.6 g of polyphosphoric acid. After having been stirred at 55° C. for 48 hours, the reaction mixture was stripped of the acetone by distillation and the residue was extracted twice with 300 ml of ether. The extract solution was washed with an aqueous sodium hydrogencarbonate solution, then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and freed from the solvent by distillation to obtain 9.5 g of a concentrate. On distillation of the concentrate, there were obtained 4.2 g of 2-(1-hydroxy-3-butenyl)furan (b.p. 78° C./10 mmHg) and 3.8 g (65.5% yield based on consumed starting material) of the intended 4-hydroxy-5-allyl-2-cyclopentenone (b.p. 97° C./0.7 mmHg). under reflux the reaction mixture was stripped of the acetone by distillation the residue was extracted twice with 300 ml of ether The extract solution was washed with an aqueous sodium hydrogencarbonate solution with saturated sodium chloride solution, dried over anhydrous sodium sulfate freed from the solvent by distillation to obtain 9.5 g of a concentrate On distillation of the concentrate

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 350 ml of a water-acetone (1:6 by volume) mixture, was dissolved 10 g of 2-(1-hydroxy-3-butenyl)furan. To the solution heated at 55° C. under reflux, was added dropwise 6.6 g of polyphosphoric acid. After having been stirred at 55° C. for 96 hours, the reaction mixture was freed from the acetone by distillation and the residue was extracted twice with 300 ml of ether. The extract solution was washed with an aqueous sodium hydrogencarbonate solution, then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and freed from the solvent by distillation to obtain 8.5 g of a concentrate. The concentrate was purified by a column chromatography using 100 g of a silica gel (Wako Gel C-200) and a toluene-ether (2:1 by volume) mixture as eluent, to obtain 4.3 g (43% yield) of 4-hydroxy-5-allyl-2-cyclopentenone. under reflux the reaction mixture was freed from the acetone by distillation the residue was extracted twice with 300 ml of ether The extract solution was washed with an aqueous sodium hydrogencarbonate solution with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate freed from the solvent by distillation to obtain 8.5 g of a concentrate The concentrate was purified by a column chromatography

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 350 ml of a water-acetone (1:6 by volume) mixture, was dissolved 10 g of 2-(1-hydroxy-3-butenyl) furan. To the solution heated at b 55° C. under reflux, was added dropwise 6.6 g of polyphosphoric acid. After having been stirred at 55° C. for 48 hours, the reaction mixture was stripped of the acetone by distillation and the residue was extracted twice with 300 ml of ether. The extract solution was washed with an aqueous sodium hydrogencarbonate solution, then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and freed from the solvent by distillation to obtain 9.5 g of a concentrate. On distillation of the concentrate, there were obtained 4.2 g of 2-(1-hydroxy-3-butenyl)furan (b.p. 78° C./10 mmHg) and 3.8 g (65.5% yield based on consumed starting material) of the intended 4-hydroxy-5-allyl-2-cyclopentenone (b.p. 97° C./0.7 mmHg). under reflux the reaction mixture was stripped of the acetone by distillation the residue was extracted twice with 300 ml of ether The extract solution was washed with an aqueous sodium hydrogencarbonate solution with saturated sodium chloride solution, dried over anhydrous sodium sulfate freed from the solvent by distillation to obtain 9.5 g of a concentrate On distillation of the concentrate

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 350 ml of a water-acetone (1:6 by volume) mixture, was dissolved 10 g of 2-(1-hydroxy-3-butenyl)furan. To the solution heated at 55° C. under reflux, was added dropwise 6.6 g of polyphosphoric acid. After having been stirred at 55° C. for 96 hours, the reaction mixture was freed from the acetone by distillation and the residue was extracted twice with 300 ml of ether. The extract solution was washed with an aqueous sodium hydrogencarbonate solution, then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and freed from the solvent by distillation to obtain 8.5 g of a concentrate. The concentrate was purified by a column chromatography using 100 g of a silica gel (Wako Gel C-200) and a toluene-ether (2:1 by volume) mixture as eluent, to obtain 4.3 g (43% yield) of 4-hydroxy-5-allyl-2-cyclopentenone. under reflux the reaction mixture was freed from the acetone by distillation the residue was extracted twice with 300 ml of ether The extract solution was washed with an aqueous sodium hydrogencarbonate solution with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate freed from the solvent by distillation to obtain 8.5 g of a concentrate The concentrate was purified by a column chromatography

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

Procedure: Reaction and after-treatment were carried out in the same manner as in Example 3 except that an equimolar amount of furfural was used in place of 5-methylfurfural, and that ammonium bromide and tetrahydrofuran were used in place of ammonium chloride and toluene, respectively, in the same weights as those of the latter, to obtain 50.6 g of the fraction of 2-(1-hydroxy-3-butenyl)-furan (content, 99.3%) (yield, 91.0%). Reaction

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 350 ml of a water-acetone (1:6 by volume) mixture, was dissolved 10 g of 2-(1-hydroxy-3-butenyl)-furan. To the solution heated at 55° C. under reflux, was added dropwise 6.6 g of polyphosphoric acid. After having been stirred at 55° C. for 48 hours, the reaction mixture was stripped of the acetone by distillation and the residue was extracted twice with 300 ml of ether. The extract solution was washed with an aqueous sodium hydrogencarbonate solution, then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and freed from the solvent by distillation to obtain 9.5 g of a concentrate. On distillation of the concentrate, there were obtained 4.2 g of 2-(1-hydroxy-3-butenyl)furan (b.p. 78° C./10 mmHg) and 3.8 g (65.5% yield based on consumed starting material) of the intended 4-hydroxy-5-allyl-2-cyclopentenone (b.p. 97° C./0.7 mmHg). under reflux the reaction mixture was stripped of the acetone by distillation the residue was extracted twice with 300 ml of ether The extract solution was washed with an aqueous sodium hydrogencarbonate solution with saturated sodium chloride solution, dried over anhydrous sodium sulfate freed from the solvent by distillation to obtain 9.5 g of a concentrate On distillation of the concentrate

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 350 ml of a water-acetone (1:6 by volume) mixture, was dissolved 10 g of 2-(1-hydroxy-3-butenyl)furan. To the solution heated at 55° C. under reflux, was added dropwise 6.6 g of polyphosphoric acid. After having been stirred at 55° C. for 96 hours, the reaction mixture was freed from the acetone by distillation and the residue was extracted twice with 300 ml of ether. The extract solution was washed with an aqueous sodium hydrogencarbonate solution, then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and freed from the solvent by distillation to obtain 8.5 g of a concentrate. The concentrate was purified by a column chromatography using 100 g of a silica gel (Wako Gel C-200) and a toluene-ether (2:1 by volume) mixture as eluent, to obtain 4.3 g (43% yield) of 4-hydroxy-5-allyl-2-cyclopentenone. under reflux the reaction mixture was freed from the acetone by distillation the residue was extracted twice with 300 ml of ether The extract solution was washed with an aqueous sodium hydrogencarbonate solution with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate freed from the solvent by distillation to obtain 8.5 g of a concentrate The concentrate was purified by a column chromatography