Ethyl Acetate → 3,7,11,15-Tetramethylhexadec-2-en-1-ol

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Reaction Steps

Lithium aluminium hydride (0.15 g, 1 mmol) is introduced over 5 minutes into a round-bottomed flask containing anhydrous ether (50 cc) at 0° C. The mixture is stirred for 10 minutes and 3,7,11,15-tetramethyl-2-hexadecenal (0.3 g, 1 mmol) is then added in solution in anhydrous ethyl ether (5 cc). The mixture is stirred for 1 hour at 0° C. and ethyl acetate (3 cc) and water (7 cc) saturated with ammonium chloride are then added. The mixture is stirred for 15 minutes and is then extracted with ethyl ether. The organic phases are dried over magnesium sulphate. After filtering and evaporating off the solvents, 3,7,11,15-tetramethyl-2-hexadecenol (or phytol) is obtained and is characterized by its infrared spectrum and its proton nuclear magnetic resonance spectrum.

Provenance & Evidence