Diethyl Ether → 2,4-Dodecadien-1-ol, (2E,4E)-

HRID 1497007Notes

Reaction equation

HRID 1497007 reaction equation
[C:1](OCC)(=[O:13])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CC(C[AlH]CC(C)C)C.C(OCC)C>CCCCCCC.[Cl-].[Na+].O>[CH2:1]([OH:13])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14487Diisobutylaluminum hydrideHCID 12387502HCID 12387502, compound

Product 1

HCID 64364912,4-Dodecadien-1-ol, (2E,4E)-

Reagents, catalysts & solvents 2

HCID 8900HeptaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-70 °C

Procedure

Under nitrogen atmosphere, (2E,4E)-ethyl dodeca-2,4-dienoate (6.1 g) was dissolved in n-heptane (120 ml) and cooled to −70° C. DIBAL-H in hexanes (82 ml) was added dropwise and the mixture was stirred at −70° C. for 45 min. Brine (60 ml) and diethyl ether (100 ml) were added and the mixture was stirred for 45 min while warming to RT. The organic layer was separated and washed with 1N HCl, dried over sodium sulfate, filtered and concentrated. A colorless liquid was isolated that solidified upon slight cooling.

Workup

  1. stirringthe mixture was stirred for 45 min
  2. temperaturewhile warming to RT
  3. customThe organic layer was separated
  4. washwashed with 1N HCl
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customA colorless liquid was isolated that solidified upon slight cooling

Sources & evidence

ORD record
ord-2bb9511455884139a9979a952666d2a9
Source dataset
uspto-grants-2015_12
Patent number
US09199948B2

Reaction notes

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