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ChemicalBook CAS DataBase List (E,Z)-2,6-Dimethyl-2,6-octadiene-1,8-diol
26488-98-2

(E,Z)-2,6-Dimethyl-2,6-octadiene-1,8-diol synthesis

12synthesis methods
-

Yield:26488-98-2 73%

Reaction Conditions:

with potassium carbonate in methanol at 20; for 4 h;

Steps:

(2E,6Z)-2,6-Dimethylocta-2,6-diene-1,8-diol (8-hydroxynerol) (4)

Potassium carbonate (114 mg, 0.88 mmol) was added to a solution of 10-hydroxynerylacetate (Z)-21 (146 mg, 0.69 mmol) in dry methanol (5 mL). After stirring at room temperature for 4 h, the mixture was diluted with water (5 mL) and extracted with diethyl ether (3 x 10 mL). The combined organic layers were washed successively with HCl (5 mL, 0.5 M), saturated NaHCO3 (5 mL) and brine (5 mL). The solution was then dried and evaporated under reduced pressure. The crude product (139 mg) was purified by chromatography on silica gel (hexanes / ethyl acetate 1 : 1) to give (E,Z)-2,6-dimethylocta-2,6-dien-1,8-diol (8-hydroxynerol) 4 as a colourless oil (86 mg, 0.50 mmol, 73%).

References:

Bogazkaya, Anna M.;Von Buehler, Clemens J.;Kriening, Sebastian;Busch, Alexandrine;Seifert, Alexander;Pleiss, Juergen;Laschat, Sabine;Urlacher, Vlada B. [Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 1347 - 1353] Location in patent:supporting information