2-pentylcyclopentane-1,3-dione

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After charging succinic acid, the mixture was allowed stand to complete generation of HCl gas. Then, thereto was added 60 g (0.4 mol) of heptanoyl chloride, and the resulting mixture was heated at 80° C. for 8 hours. Since heptanoyl chloride is also fuming (HCl gas), measures were taken against corrosion of equipment in the peripheral environment at the time of weighing, but it was with difficulty. The mixture was cooled, poured onto 60 g of ice, and maintained at −10° C. for 10 hours, depositing a product as a solid. The product was subjected to suction filtration, washed with 10% NaCl water and toluene (20 ml×3 times), and dried, yielding 8.4 g (0.05 mol) of 2-pentyl-1,3-cyclopentanedione (a compound in which R1 represents an n-pentyl group in the above formula (3)). Yields were 20.8%, 50.0%, and 12.5% relative to AlCl3, succinic acid, and heptanoyl chloride, respectively. Simultaneously, wastewater containing a large amount of an aluminum-based and a chlorine-based compound was byproduced. The mixture was cooled maintained at −10° C. for 10 hours The product was subjected to suction filtration washed with 10% NaCl water and toluene (20 ml×3 times) dried

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 32.5 g (0.19 mol) of 2-n-pentyl-1,3-cyclopentanedione was added 650 ml of methanol containing 1 wt % of hydrogen chloride (prepared by preliminarily blowing hydrogen chloride therein), followed by heating under reflux for 5 hours and cooling to 25° C. Then, thereto was gradually added 15.4 g of sodium hydrogencarbonate followed by stirring for 30 minutes at 25° C. Methanol was distilled off in vacuo and then 200 mL of water and 200 mL of isobutanol were added. The resulting mixture was stirred for 10 minutes at 25° C. and then allowed to stand to separate the organic phase. Isobutanol in the organic phase was distilled off, yielding 2-pentyl-3-methoxy-2-cyclopentenone (a compound in which R20 represents an n-pentyl group, and R21 represents a methyl group in the above formula (14)). Gas chromatographic analysis showed that the yield of 2-pentyl-3-methoxy-2-cyclopentenone relative to 2-n-pentyl-1,3-cyclopentanedione was 80%. by heating under reflux for 5 hours Methanol was distilled off in vacuo 200 mL of water and 200 mL of isobutanol were added The resulting mixture was stirred for 10 minutes at 25° C. to separate the organic phase Isobutanol in the organic phase was distilled off

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 32.5 g (0.19 mol) of 2-n-pentyl-1,3-cyclopentanedione was added 650 ml of methanol containing 1 wt % of hydrogen chloride (prepared by preliminarily blowing hydrogen chloride therein), followed by heating under reflux for 5 hours and cooling to 25° C. Then, thereto was gradually added 15.4 g of sodium hydrogencarbonate followed by stirring for 30 minutes at 25° C. Methanol was distilled off in vacuo and then 200 mL of water and 200 mL of isobutanol were added. The resulting mixture was stirred for 10 minutes at 25° C. and then allowed to stand to separate the organic phase. Isobutanol in the organic phase was distilled off, yielding 2-pentyl-3-methoxy-2-cyclopentenone (a compound in which R20 represents an n-pentyl group, and R21 represents a methyl group in the above formula (14)). Gas chromatographic analysis showed that the yield of 2-pentyl-3-methoxy-2-cyclopentenone relative to 2-n-pentyl-1,3-cyclopentanedione was 80%. by heating under reflux for 5 hours Methanol was distilled off in vacuo 200 mL of water and 200 mL of isobutanol were added The resulting mixture was stirred for 10 minutes at 25° C. to separate the organic phase Isobutanol in the organic phase was distilled off

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After charging succinic acid, the mixture was allowed stand to complete generation of HCl gas. Then, thereto was added 60 g (0.4 mol) of heptanoyl chloride, and the resulting mixture was heated at 80° C. for 8 hours. Since heptanoyl chloride is also fuming (HCl gas), measures were taken against corrosion of equipment in the peripheral environment at the time of weighing, but it was with difficulty. The mixture was cooled, poured onto 60 g of ice, and maintained at −10° C. for 10 hours, depositing a product as a solid. The product was subjected to suction filtration, washed with 10% NaCl water and toluene (20 ml×3 times), and dried, yielding 8.4 g (0.05 mol) of 2-pentyl-1,3-cyclopentanedione (a compound in which R1 represents an n-pentyl group in the above formula (3)). Yields were 20.8%, 50.0%, and 12.5% relative to AlCl3, succinic acid, and heptanoyl chloride, respectively. Simultaneously, wastewater containing a large amount of an aluminum-based and a chlorine-based compound was byproduced. The mixture was cooled maintained at −10° C. for 10 hours The product was subjected to suction filtration washed with 10% NaCl water and toluene (20 ml×3 times) dried

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 32.5 g (0.19 mol) of 2-n-pentyl-1,3-cyclopentanedione was added 650 ml of methanol containing 1 wt % of hydrogen chloride (prepared by preliminarily blowing hydrogen chloride therein), followed by heating under reflux for 5 hours and cooling to 25° C. Then, thereto was gradually added 15.4 g of sodium hydrogencarbonate followed by stirring for 30 minutes at 25° C. Methanol was distilled off in vacuo and then 200 mL of water and 200 mL of isobutanol were added. The resulting mixture was stirred for 10 minutes at 25° C. and then allowed to stand to separate the organic phase. Isobutanol in the organic phase was distilled off, yielding 2-pentyl-3-methoxy-2-cyclopentenone (a compound in which R20 represents an n-pentyl group, and R21 represents a methyl group in the above formula (14)). Gas chromatographic analysis showed that the yield of 2-pentyl-3-methoxy-2-cyclopentenone relative to 2-n-pentyl-1,3-cyclopentanedione was 80%. by heating under reflux for 5 hours Methanol was distilled off in vacuo 200 mL of water and 200 mL of isobutanol were added The resulting mixture was stirred for 10 minutes at 25° C. to separate the organic phase Isobutanol in the organic phase was distilled off