trans-2-Octen-1-ol synthesis
- Product Name:trans-2-Octen-1-ol
- CAS Number:18409-17-1
- Molecular formula:C8H16O
- Molecular Weight:128.21
71-36-3
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18409-17-1
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Yield:18409-17-1 49%
Reaction Conditions:
with n-butyllithium in hexane
Steps:
17 EXAMPLE 17
EXAMPLE 17 A hexane solution of n-butyllithium (2.1 mmol) was cooled at 0° C. under the argon atmosphere. A hexane solution of n-butanol (75.9 mg; 1.0 mmol) was added dropwise thereto and stirred. To the resulting solution, there was further added dropwise a hexane solution of 3,4-epoxy-butene-1 (70.0 mg; 1 mmol), and after the addition was completed, the resulting mixture was cooled at 0° C. for 1 hour and at room temperature for 30 minutes, followed by the usual work up. Removal of the solvent and distillation of the residue gave 63 mg of 2-octen-1-ol (yield, 49%). After acetylation of the thus obtained product, gas chromatographic analysis (PEG 20M, 4 m) was effected at a temperature of 130° C. The retention times of Z-isomer and E-isomer were respectively 13.7 minutes and 14.7 minutes, and the Z/E ratio was 89.1/10.9. NMR spectrum (CDCl3) δ ppm: Z-acetate: 5.59 (2H, multiplet), 4.62 (2H, doublet, J=5.4 Hz), 2.60 (3H, singlet), 2.06 (2H, multiplet), 1.31 (6H, multiplet), 0.89 (3H, multiplet); E-acetate: 5.66 (2H, multiplet), 4.50 (2H, doublet, J=5.6 Hz), 2.06 (3H, singlet), 2.06 (2H, multiplet), 1.31 (6H, multiplet), 0.89 (3H, multiplet). The 13 NMR spectral data of 9-octen-1-ol was as follows: (CDCl3) δ ppm: Z-acetate: 60.4 (C-1), 135.4 (C-2), 123.4 (C-3), 27.5 (C-4), 29.1 (C-5), 31.4 (C-6),. 22.5 (C-7), 14.0 (C-8); E-acetate: 65.2 (C-1), 136.6 (C-2), 123.9 (C-3), 33.2 (C-4), 28.6 (C-5), 31.4 (C-6), 22.5 (C-7), 13.9 (C-8), when the carbon atoms were numbered in the following manner: STR10
References:
Sumitomo Chemical Company, Limited US5004843, 1991, A
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18409-17-1
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2548-87-0
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18409-17-1
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88088-16-8
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18409-17-1
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