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

HRID 2352388Notes

Reaction equation

HRID 2352388 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([CH2:12][CH2:13][CH2:14][CH:15]([CH3:27])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:26])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:9][CH:10]=[O:11].C(OCC)(=O)C.[Cl-].[NH4+]>C(OCC)C.O>[CH3:7][C:8]([CH2:12][CH2:13][CH2:14][CH:15]([CH3:27])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:26])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:9][CH2:10][OH:11].[CH3:25][CH:23]([CH2:22][CH2:21][CH2:20][C@H:19]([CH2:18][CH2:17][CH2:16][C@H:15]([CH2:14][CH2:13][CH2:12]/[C:8](=[CH:9]/[CH2:10][OH:11])/[CH3:7])[CH3:27])[CH3:26])[CH3:24]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 542561913,7,11,15-Tetramethylhexadec-2-enal

Product 2

HCID 1453863,7,11,15-Tetramethylhexadec-2-en-1-olHCID 5280435Phytol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  1. stirringThe mixture is stirred for 1 hour at 0° C.
  2. stirringThe mixture is stirred for 15 minutes
  3. extractionis then extracted with ethyl ether
  4. dry with materialThe organic phases are dried over magnesium sulphate
  5. filtrationAfter filtering
  6. customevaporating off the solvents

Sources & evidence

ORD record
ord-489166d74a7649b695fce5ceb47477d6
Source dataset
uspto-grants-1989_10
Patent number
US04876370

Reaction notes

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