ChemicalBook CAS DataBase List 9-Heptadecanol

9-Heptadecanol synthesis

14synthesis methods

Product Name:9-Heptadecanol
CAS Number:624-08-8
Molecular formula:C17H36O
Molecular Weight:256.47

17049-49-9
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109-94-4 Synthesis

109-94-4
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624-08-8
131 suppliers
$113.00/1g

Yield:624-08-8 89.3%

Reaction Conditions:

Stage #1:octylmagnesium bromide;formic acid ethyl ester in tetrahydrofuran at 20;
Stage #2: with ammonium chloride in tetrahydrofuran;methanol;water

Steps:

4.2.1. Heptadecane-9-ol (1)
A solution of ethyl formate (10 g, 135 mmol) in dry THF (80 mL) was added dropwise to a fresh solution of octyl magnesium bromide, which was prepared from 1-bromooctane (58 g, 300 mmol) and magnesium (8.15 g, 340 mmol) in 150 mL dry THF. After then, the reaction mixture was stirred overnight at room temperature. Next, the reaction mixture was quenched by the addition of MeOH, followed by saturated aqueous NH₄Cl. The crude compound was extracted three times with ethyl acetate. The combined organic fractions were washed with brine and dried over MgSO₄. After removal of the solvent, the residue was purified by recrystalization from acetonitrile to afford heptadecane-9-ol (1) as white solids (30.91 g, 89.3%). ¹H NMR (300 MHz, CDCl₃), δ (ppm): 3.58 (m, 1H), 1.43-1.25 (m, 29H), 0.88 (t, J=6.6 Hz, 6H).

References:

Sahu, Duryodhan;Padhy, Harihara;Patra, Dhananjaya;Yin, Jen-Fu;Hsu, Ying-Chan;Lin, Jiann-T'Suen;Lu, Kuang-Lieh;Wei, Kung-Hwa;Lin, Hong-Cheu [Tetrahedron,2011,vol. 67,# 2,p. 303 - 311] Location in patent:experimental part

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