(Z,Z)-11,13-Hexadecadienyl acetate synthesis
- Product Name:(Z,Z)-11,13-Hexadecadienyl acetate
- CAS Number:118744-50-6
- Molecular formula:C18H32O2
- Molecular Weight:280.45
Yield:118744-50-6 98%
Reaction Conditions:
with pyridine in dichloromethane at 0; for 4 h;
Steps:
(11Z,13Z)-hexadecadienyl acetate (3):
A total of 0.47 g (6 mmol) of pyridine was added to a solutionof 1.19 g (5 mmol) of 2 in 10 mL of CH2Cl2 at 0 °C, followed by 0.61 g (6 mmol) of acetic anhydride.The mixture was stirred for 4 h and washed with water. The organic was then concentrated to removethe solvent, and the crude was puried using ash chromatography on silica gel using hexane-ethylacetate (30:1, v/v) as an eluent to provide 1.37 g (4.9 mmol, 98%) of 3 as a colorless liquid. 1H-NMR(500 MHz, CDCl3) δ 1.01 (3H, m), 1.31 (16H, m), 1.62 (2H, m), 2.04 (3H, s), 2.16-2.19 (2H, m), 4.05 (2H,t, J = 6.5 Hz), 5.42-5.47 (2H, m), 6.21-6.28 (2H, m); 13C-NMR (125 MHz, CDCl3) δ 171.3, 133.6, 132.1,123.4, 123.0, 64.7, 32.9, 29.7, 29.6, 29.5, 29.5, 29.3, 29.3, 28.6, 27.5, 25.9, 21.0, 14.2. GC-MS: tR: 21.97 min;MS of 3 (70 eV, EI): 280.
References:
Liu, Fu;Kong, Xiangbo;Zhang, Sufang;Zhang, Zhen [Molecules,2019,vol. 24,# 9,art. no. 1781]
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