tetradecane-7,8-diol synthesis

9synthesis methods

Product Name:tetradecane-7,8-diol
CAS Number:16000-65-0
Molecular formula:C14H30O2
Molecular Weight:230.39

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Yield:16000-65-0 88%

Reaction Conditions:

with formic acid;dihydrogen peroxide at 20 - 50;Cooling;

Steps:

2

EXAMPLE 2[0061 ] This Example serves to illustrate synthesis and isolation of a diol, and subsequent esterification of said diol, en route to synthesis of a diester species, in accordance with some embodiments of the present invention.Diol Preparation and Isolation[0062] In a 3-neck 1 mL reaction flask equipped with an overhead stirrer and an ice bath, 75 mL of 30% hydrogen peroxide were added to 300 mL of 96% formic acid. To this mixture, 100 grams (0.51 mole) of 7-tetradecene (purchased from Aldrich Chemical Co.) was added slowly over a 30 minote period via a dropping funnel. Once the addition of the olefin was complete, the reaction was allowed to stir while cooling with the ice-bath to prevent rise in the temperature above 40-50°C for 2 hrs. The ice-bath was then removed and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated with a rotary evaporator in a hot water bath at -30 torr to remove most of the water and formic acid. Then, 100 mL of ice-cold 1 M solution of sodium hydroxide was added very slowly (in small portions) and carefully to the remaining residue of the reaction. Once all the sodium hydroxide solution was added, the mixture was allowed to stir for an additional 45-60 minutes at room temperature. The mixture was diluted with 500 mL ethyl acetate and transferred to a separatory runnel. The organic layer was sequestered and the aqueous layer was extracted 3 times (3x200 mL) with ethyl acetate. The ethyl acetate extracts were combined and dried over anhydrous MgSO₄. Filtration, followed by concentration on a rotary evaporator at reduced pressure in a hot water bath gave the desired diol as white powder in 88% yield (95 grams). The produced and isolated diol (tetradecane- 7,8-diol) was characterized by nuclear magnetic resonance (NMR) spectroscopy and gas-chromatography/mass spectrometry (GC/MS).

References:

WO2009/142922,2009,A1 Location in patent:Page/Page column 14-15