2-(1-hydroxyheptyl)cyclopentan-1-one

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

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

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

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

Procedure: In a 100 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer were placed 2-(1-hydroxyheptyl)cyclopentanone (40 g) synthesized in Reference Example 3, bromine (0.4 g) and n-octane (10 ml), and water was removed under refluxing, followed by 4 hours of the reaction at 120° C. The reaction mixture was washed with water and the layers were separated from each other. The resulting organic layer was washed with saturated brine and separated. The organic layer was evaporated on a rotary evaporator under reduced pressure to recover n-octane, whereby a crude product (39 g) was obtained. The product was distilled using a Claisen distillation apparatus to obtain 32 g of 2-heptyl-2-cyclopentenone (boiling point: 111° C./900 Pa; GC purity: 97.8%). In a 100 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer was removed under refluxing followed by 4 hours of the reaction at 120° C The reaction mixture was washed with water the layers were separated from each other The resulting organic layer was washed with saturated brine separated The organic layer was evaporated on a rotary evaporator under reduced pressure to recover n-octane, whereby a crude product (39 g) was obtained The product was distilled a Claisen distillation apparatus

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

Procedure: In a 100 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer were placed 2-(1-hydroxyheptyl)cyclopentanone (40 g) synthesized in Reference Example 3, bromine (0.4 g) and n-octane (10 ml), and water was removed under refluxing, followed by 4 hours of the reaction at 120° C. The reaction mixture was washed with water and the layers were separated from each other. The resulting organic layer was washed with saturated brine and separated. The organic layer was evaporated on a rotary evaporator under reduced pressure to recover n-octane, whereby a crude product (39 g) was obtained. The product was distilled using a Claisen distillation apparatus to obtain 32 g of 2-heptyl-2-cyclopentenone (boiling point: 111° C./900 Pa; GC purity: 97.8%). In a 100 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer was removed under refluxing followed by 4 hours of the reaction at 120° C The reaction mixture was washed with water the layers were separated from each other The resulting organic layer was washed with saturated brine separated The organic layer was evaporated on a rotary evaporator under reduced pressure to recover n-octane, whereby a crude product (39 g) was obtained The product was distilled a Claisen distillation apparatus

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

Procedure: In a 300 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer were placed 2-(1-hydroxyheptyl)cyclopentanone (70 g) synthesized in Reference Example 3, oxalic acid (0.7 g) and toluene (140 ml), and the whole was refluxed to allow dehydration to proceed. The formed water was removed and the reaction was continued until water was not formed any more (about 2.5 hours). The reaction mixture was washed with water and the layers were separated from each other. Further, the resulting organic layer was washed with saturated brine and separated. The organic layer was evaporated on a rotary evaporator under reduced pressure to recover toluene and unreacted cyclopentanone, whereby a crude product (63 g) was obtained. The product was distilled using a Claisen distillation apparatus to obtain 55 g of 2-heptylidenecyclopentanone (boiling point: 56° C./400 Pa; GC purity: 98.5%). In a 300 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer the whole was refluxed The formed water was removed was not formed any more (about 2.5 hours) The reaction mixture was washed with water the layers were separated from each other Further, the resulting organic layer was washed with saturated brine separated The organic layer was evaporated on a rotary evaporator under reduced pressure to recover toluene and unreacted cyclopentanone, whereby a crude product (63 g) was obtained The product was distilled a Claisen distillation apparatus

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 2-litter four-neck flask fitted with a thermometer, a reflux condenser and a stirrer were added sodium hydroxide (3.2 g) and water (300 ml). Then, a mixture of heptanal (114 g) and cyclopentanone (152 g) was added dropwise thereto under stirring at 0-5° C. over a period of 2 hours. After the addition, the reaction mixture was stirred at room temperature for 1 hour to complete the reaction. Hexane (150 ml) was added to the reaction mixture and the layers were separated from each other. The resulting organic layer was washed with an aqueous solution (200 ml) of acetic acid (1 g) and separated. Then, the resulting organic layer was washed with saturated brine and separated. The organic layer was evaporated on a rotary evaporator under reduced pressure to recover hexane and unreacted cyclopentanone, whereby a product (202 g) was obtained. The product was distilled using a Claisen distillation apparatus to obtain 154 g of 2-(1-hydroxyheptyl)cyclopentanone (boiling point: 112-114° C./666 Pa; GC purity: 92%). The remaining 8% was 2-heptylidenecyclopentanone which is a dehydration product. Into a 2-litter four-neck flask fitted with a thermometer, a reflux condenser and a stirrer was added dropwise After the addition the reaction mixture was stirred at room temperature for 1 hour the reaction the layers were separated from each other The resulting organic layer was washed with an aqueous solution (200 ml) of acetic acid (1 g) separated Then, the resulting organic layer was washed with saturated brine separated The organic layer was evaporated on a rotary evaporator under reduced pressure to recover hexane and unreacted cyclopentanone, whereby a product (202 g) was obtained The product was distilled a Claisen distillation apparatus

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 2-litter four-neck flask fitted with a thermometer, a reflux condenser and a stirrer were added sodium hydroxide (3.2 g) and water (300 ml). Then, a mixture of heptanal (114 g) and cyclopentanone (152 g) was added dropwise thereto under stirring at 0-5° C. over a period of 2 hours. After the addition, the reaction mixture was stirred at room temperature for 1 hour to complete the reaction. Hexane (150 ml) was added to the reaction mixture and the layers were separated from each other. The resulting organic layer was washed with an aqueous solution (200 ml) of acetic acid (1 g) and separated. Then, the resulting organic layer was washed with saturated brine and separated. The organic layer was evaporated on a rotary evaporator under reduced pressure to recover hexane and unreacted cyclopentanone, whereby a product (202 g) was obtained. The product was distilled using a Claisen distillation apparatus to obtain 154 g of 2-(1-hydroxyheptyl)cyclopentanone (boiling point: 112-114° C./666 Pa; GC purity: 92%). The remaining 8% was 2-heptylidenecyclopentanone which is a dehydration product. Into a 2-litter four-neck flask fitted with a thermometer, a reflux condenser and a stirrer was added dropwise After the addition the reaction mixture was stirred at room temperature for 1 hour the reaction the layers were separated from each other The resulting organic layer was washed with an aqueous solution (200 ml) of acetic acid (1 g) separated Then, the resulting organic layer was washed with saturated brine separated The organic layer was evaporated on a rotary evaporator under reduced pressure to recover hexane and unreacted cyclopentanone, whereby a product (202 g) was obtained The product was distilled a Claisen distillation apparatus

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