2-(1-hydroxyhexyl)cyclopentan-1-one

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: In a 30 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer were placed 2-(1-hydroxyhexyl)cyclopentanone (20 g) synthesized in Reference Example 2 and iodine (5 mg), followed by 6 hours of the reaction at 150° C. The crude product was purified by column chromatography (hexane/ethyl acetate: 95/5) to obtain 15.3 g of 2-hexyl-2-cyclopentenone (GC purity: 99.1%). In a 30 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer followed by 6 hours of the reaction at 150° C The crude product was purified by column chromatography (hexane/ethyl acetate: 95/5)

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

実験手順: In a 300 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer were placed 2-(1-hydroxyhexyl)cyclopentanone (85 g) synthesized in Reference Example 2, oxalic acid (1.0 g) and toluene (150 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 3 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 (78 g) was obtained. The product was distilled using a Claisen distillation apparatus to obtain 67 g of 2-hexylidenecyclopentanone (boiling point: 92° C./533 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 3 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 (78 g) was obtained The product was distilled a Claisen distillation apparatus

反応条件: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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 hexanal (100 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 then separated. The resulting organic layer was further 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 crude product (188 g) was obtained. The product was distilled using a Claisen distillation apparatus to obtain 142 g of 2-(1-hydroxyhexyl)cyclopentanone (boiling point: 107-108° C./666 Pa; GC purity: 94%). The remaining 6% was 2-hexylidenecyclopentanone 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 The resulting organic layer was further 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 crude product (188 g) was obtained The product was distilled a Claisen distillation apparatus