Diethyl Ether → geranylcitronellol

HRID 1589533Notes

Reaction equation

HRID 1589533 reaction equation
C(OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:12][CH:13]([CH2:18][CH2:19]/[CH:20]=[C:21](\[CH3:33])/[CH2:22][CH2:23]/[CH:24]=[C:25](\[CH3:32])/[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[CH2:14][C:15](O)=[O:16].C(OCC)(=O)C>O>[CH3:12][CH:13]([CH2:18][CH2:19]/[CH:20]=[C:21](\[CH3:33])/[CH2:22][CH2:23]/[CH:24]=[C:25](\[CH3:32])/[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[CH2:14][CH2:15][OH:16]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 12837064(E,E)-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 5365870geranylcitronellol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

To 150 ml. of anhydrous diethyl ether there was added 1.9 g. of lithium aluminum hydride. To the mixture was dropwise added, under stirring and at 10° C., 1.53 g. of the carboxylic acid compound obtained in Example 1. The resulting mixture was then stirred at room temperature for 1 hour, and 1 ml. of ethyl acetate and 1 ml. of water were then added thereto. The mixture was subsequently washed with water and dried. The solvent was removed by evaporation and the resulting residual oil was purified by silica gel column chromatography to obtain 13.8 g. of the desired oily product.

Workup

  1. additionTo the mixture was dropwise added
  2. stirringThe resulting mixture was then stirred at room temperature for 1 hour
  3. washThe mixture was subsequently washed with water
  4. customdried
  5. customThe solvent was removed by evaporation
  6. customthe resulting residual oil was purified by silica gel column chromatography
  7. customto obtain 13.8 g

Sources & evidence

ORD record
ord-d27af73eb17241988ee4120a30322015
Source dataset
uspto-grants-1986_02
Patent number
US04571408

Reaction notes

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