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ChemicalBook CAS DataBase List 1,14-TETRADECANEDIOL

1,14-TETRADECANEDIOL synthesis

6synthesis methods
-

Yield:19812-64-7 95%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0; for 21 h;Inert atmosphere;Reflux;

Steps:

1,14-Tetradecanediol [HO(CH2)14OH]

A 1 M solution of LAH in THF (60 mL, 60 mmol) was added to anhydrous THF (50 mL) in a flask preflushed with argon at 0 °C. MeO2C(CH2)12CO2Me (3.44 g, 12 mmol) in anhydrous THF (30mL) was then added dropwise and the mixture was allowed to stir for 5 h and heated under reflux for 16 h. The reaction mixture was cooled to r.t., quenched with EtOAc (15 mL) then H2O (50 mL) until no more gas evolved. The mixture was shaken with a 1 M aqs olution of sodium potassium tartrate (100 mL) for 5 min. The top organic layer was collected and evaporated to afford a white solid;yield: 2.62 g (95%). The spectroscopic properties were identical tothose previously published.

References:

Curvey, Nichole S.;Luderer, Sarah E.;Walker, John K.;Gokel, George W. [Synthesis,2014,vol. 46,# 20,art. no. SS-2014-M0201-OP,p. 2771 - 2779]

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