Compound having cyclopropane ring and fragrance composition and/or fragrance composition containing same
A technology of compound and composition, which is applied in the field of fragrance composition, can solve the problem of no fragrance, etc., and achieve the effects of excellent fragrance imparting, high liking, diffusivity and residual fragrance
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Embodiment 1
[0045] Synthesis of 1-methyl-2-(1-phenylethyl)cyclopropylmethanol
[0046] [chemical 7]
[0047]
[0048] Under a nitrogen atmosphere, a toluene solution of diethylzinc (concentration 15% by weight, 37.9 g, 46.0 mmol) was added to a 200 ml flask equipped with a stirring device, a dropping funnel, and a thermometer, and cooled to -20°C. Chloroiodomethane (16.22 g, 92.0 mmol) was added to the dropping funnel, and added dropwise while maintaining -15 to -20°C. After the dropwise addition, stir at -10 to -15°C for 30 minutes, cool to -25°C, and drop (E)-2-methyl-4-phenylpentadiene in the range of -20 to -25°C -2-en-1-ol (4.11 g, 23.3 mmol) for 60 minutes. After completion of the dropwise addition, stirring was continued for 60 minutes at -15 to -25°C. Next, after adding 20% sulfuric acid aqueous solution (17.0 ml) and stirring for 10 minutes, the aqueous layer was liquid-separated. The organic layer was washed twice with water (20 ml), and the solvent was recovered under ...
Embodiment 2
[0064] Synthesis of 1-methyl-2-(1-phenylethyl)cyclopropylmethanol
[0065] [chemical 8]
[0066]
[0067] Under a nitrogen atmosphere, a toluene solution of diethylzinc (concentration 15% by weight, 69.8 g, 84.8 mmol) was added to a 100 ml flask equipped with a stirring device, a dropping funnel, and a thermometer, and cooled to -20°C. Chloroiodomethane (29.9 g, 169.6 mmol) was added to the dropping funnel, and added dropwise while maintaining -15 to -20°C. After the dropwise addition, stir at -10 to -15°C for 30 minutes, then cool to -25°C, and drop (Z)-2-methyl-4-phenylpenta- 2-en-1-ol (7.59 g, 42.4 mmol) 60 minutes. After completion of the dropwise addition, stirring was continued for 60 minutes at -15 to -25°C. Next, after adding 20% sulfuric acid aqueous solution (31.3 ml) and stirring for 10 minutes, the aqueous layer was liquid-separated. The organic layer was washed twice with water (30 ml), and the solvent was recovered under reduced pressure to obtain a conc...
Embodiment 3
[0083] Synthesis of (1S*, 2S*)-1-methyl-2-[(R*)-1-phenylethyl]cyclopropanecarbaldehyde
[0084] [chemical 9]
[0085]
[0086]Under a nitrogen atmosphere, add [(1S*, 2S*)-1-methyl-2-((R*)-1-phenylethyl) to a 100ml flask equipped with a stirring device, dropping funnel, and thermometer Cyclopropyl]methanol (1.02g, 5.37mmol) and potassium bromide (0.36g), 2,2,6,6-tetramethylpiperidine 1-oxyl radical (0.085g) and toluene (10ml), Cool to 0 °C. A sodium hypochlorite aqueous solution (concentration: about 13.5%, 5.0 g, 9.1 mmol) was added to the dropping funnel, and added dropwise while maintaining 0°C. After completion of the dropwise addition, the temperature was raised to 18° C. over 60 minutes. Thereafter, the aqueous layer was separated, the organic layer was washed with 10% aqueous sodium thiosulfate solution and water, and the solvent was recovered under reduced pressure to obtain the concentrated residue (1S*, 2S*)-1-methyl-2-[ (R*)-1-Phenylethyl]cyclopropanecarbaldeh...
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