ChemicalBook CAS DataBase List 1-UNDECANOL

1-UNDECANOL synthesis

13synthesis methods

Product Name:1-UNDECANOL
CAS Number:112-42-5
Molecular formula:C11H24O
Molecular Weight:172.31

By reduction of the corresponding aldehyde.

112-43-6 Synthesis

112-43-6
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112-42-5
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Yield:112-42-5 94%

Reaction Conditions:

with sodium tetrahydroborate;ruthenium(III) trichloride hydrate in 1-methyl-pyrrolidin-2-one;water at 0; for 1 h;chemoselective reaction;Solvent;

Steps:

General procedure for alkene reduction
General procedure: To a 15-mL 1-neck reaction flask fitted with a glass stopper [Note: A larger-scale reaction may require the use of a pressure vessel and/or addition of NaBH4 in small portions.] were added a small spin bar, 0.18-0.20 mmol of substrate, 0.60 mL of 5:1 (v/v) [10:1 (v/v) in Table 1, entry 3] liquid amide(s)/H2O, and 7.0 mg (0.034 mmol) of ruthenium(III) chloride hydrate (Sigma-Aldrich Catalog No. 206229). After cooling the latter mixture to 0 C (external ice-H2O bath), 9.0 mg (0.24 mmol) of NaBH4 powder was added in one portion; and the mixture was subsequently stirred at 0 C for 60 min. The reaction was then quenched by addition of 2.0 mL of 2 M aqueous HCl to the reaction flask, followed by 1.0 mL of pentane and subsequent stirring of the mixture at 0 C for 15 min. The product was then isolated by dilution of the reaction mixture with 10 mL of 4:1 (v/v) pentane/dichloromethane; and solid material was removed by filtration through a small pad of Hyflo Super-Cel filtering aid. After dilution of the filtrate with 10 mL of pentane, removal of the liquid amide(s) was accomplished by washing the filtrate with 10% (w/v) aqueous NaCl (4 15 mL portions). The organic layer was subsequently dried over anhydrous MgSO4, filtered, and the volatile organic solvents were removed by evaporation at reduced pressure.

References:

Babler, James H.;Ziemke, David W.;Hamer, Robert M. [Tetrahedron Letters,2013,vol. 54,# 13,p. 1754 - 1757]

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