ChemicalBook CAS DataBase List (5Z)-5-Tetradecenoic acid

(5Z)-5-Tetradecenoic acid synthesis

8synthesis methods

Product Name:(5Z)-5-Tetradecenoic acid
CAS Number:5684-70-8
Molecular formula:C14H26O2
Molecular Weight:226.35

124-19-6 Synthesis

124-19-6
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$7.00/25g

17814-85-6 Synthesis

(4-Carboxybutyl)triphenylphosphonium bromide

17814-85-6
391 suppliers
$8.00/5g

5684-70-8
9 suppliers
$185.00/10mg

Yield:5684-70-8 84%

Reaction Conditions:

Stage #1: (4-carboxybutyl)triphenylphosphonium bromidewith sodium hexamethyldisilazane in tetrahydrofuran at 20; for 2 h;Inert atmosphere;
Stage #2: nonan-1-al in tetrahydrofuran at 20; for 3 h;stereoselective reaction;Wittig reaction;

Steps:

3.2.5. General procedure for the synthesis of unsaturated carboxylic acids (6)

General procedure: To a stirring suspension of phosphonium salts (5a-e) (1 equiv) in THF (250 mL) was added slowly 40% solution of sodium hexamethyldisilylamide (2 equiv) THF at room temperature in argon and stirring continued for 2 h. Aldehyde (1 equiv) was dissolved in THF (25 mL) and introduced drop wise. The mixture was stirred for further 3 h and then poured into 150 mL of water to get a clear solution. The resulting solution was concentrated in vacuum and the residue was extracted with diethyl ether (3 x 250 mL). The aqueous layer was acidified with 10% HCl and extracted with ether (3 x 200 mL). The organic layer obtained from the aqueous extract was dried and concentrated to afford the corresponding unsaturated carboxylic acids (6a-m).

References:

Wube, Abraham A.;Hüfner, Antje;Thomaschitz, Christina;Blunder, Martina;Kollroser, Manfred;Bauer, Rudolf;Bucar, Franz [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 1,p. 567 - 579] Location in patent:experimental part

124-19-6 Synthesis

124-19-6
352 suppliers
$7.00/25g

17814-85-6 Synthesis

17814-85-6
391 suppliers
$8.00/5g