ChemicalBook CAS DataBase List 9-hydroxystearic acid

9-hydroxystearic acid synthesis

12synthesis methods

Product Name:9-hydroxystearic acid
CAS Number:3384-24-5
Molecular formula:C18H36O3
Molecular Weight:300.48

112-80-1 Synthesis

112-80-1
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3384-24-5
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Yield:3384-24-5 42%

Reaction Conditions:

Stage #1: cis-Octadecenoic acidwith borane-THF in tetrahydrofuran at 20;
Stage #2: with water;dihydrogen peroxide;sodium hydroxide in tetrahydrofuran at 0 - 20; for 1 h;

Steps:

1.1 1. Synthesis of 9-hydroxy-octadecanoic acid.

Oleic acid (0.1 g, 0.5 mmol) was reacted with borane·tetrahydrofuran-complex (0.4 mL, 0.9 M, 0.3 mmol borane) in tetrahydrofuran (3 mL).The solution was stirred at room temperature overnight.Water (1.0 mL) was added to destroy the borane.Then, the solution was cooled to 0 ° C and 3N NaOH solution (2 mL) was added dropwise.And 30% H 2 O 2 - solution (6 mL).After reacting for 1 hour at room temperature,Water (10 mL) and saturated NaCl were added and the aqueous extracted with EtOAc EtOAc.The ethyl acetate layer was dried (MgSO4)EtOAcEtOAcThe residue was purified by flash chromatography (chloroform / methanol 200:1, v / v)A white powder of 9-hydroxy-octadecanoic acid (42.2 mg, 42%) was obtained.Rf = 0.3 (chloroform / methanol 10:1, v / v).

References:

CN110041221,2019,A Location in patent:Paragraph 0056; 0063-0064