Water → (E)-Tetradec-2-en-1-ol

HRID 2210862Notes

Reaction equation

HRID 2210862 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][CH2:11][CH3:12])(=O)C.O.O1[CH2:18][CH2:17][CH2:16][CH2:15]1>>[CH2:11]([OH:10])/[CH:12]=[CH:15]/[CH2:16][CH2:17][CH2:18][CH2:15][CH2:16][CH2:17][CH2:18][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 5353006(E)-Tetradec-2-en-1-ol

Procedure

To dodecyl aldehyde (5.0 g) dissolved in methylene chloride was added (carbomethoxymethylene)triphenylphosphorane (9.1 g), and the mixture was stirred for 2 hours. The reaction mixture was concentrated and subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to 20:1) to give the methyl ester of trans-2-tetradecenoic acid (5.2 g). To the methyl ester dissolved in tetrahydrofuran was added lithium aluminium hydride (0.9 g) under ice-cooling, and the mixture was stirred for 1 hour. The reaction mixture was distributed into ethyl acetate and water, and the ethyl acetate layer was dried, concentrated and subjected to chromatography on a silica gel column with an eluent system of n-hexane-ethyl acetate (50:1) to give trans-2-tetradecenol (3.2 g). To the solution of the trans-2-tridecenol in methylene chloride were added pyridinium chlorochromate (3.5 g) and Celite (5.0 g), and the mixture was stirred. The reaction mixture was filtered and concentrated to give trans-2-tetradecenal (2.3 g).

Workup

  1. temperaturecooling
  2. dry with materialthe ethyl acetate layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-88a4cc2a15f2494e87cb8875b92b0cbe
Source dataset
uspto-grants-1995_10
Patent number
US05461036

Reaction notes

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