tert-Butanol → HCID 53669934, compound

HRID 364250Notes

Reaction equation

HRID 364250 reaction equation
[C:1](O)([CH3:4])([CH3:3])C.C[C:7]([CH3:10])([O-])[CH3:8].[K+]>C1COCC1.O>[CH2:4]=[CH:1][CH:3]=[CH:10][CH2:7][CH2:8][CH2:8][CH2:7][CH:10]=[CH:3][CH:1]=[CH2:4]

Participants

5

Reactant 2

HCID 6386tert-Butanol2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 53669934HCID 53669934, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The latter compound (2.0 g) was dissolved in 50 mL of 1:4 THF:tert-butanol and added dropwise to an ice cold solution of potassium tert-butoxide (3.00 g) in 100 mL of 1:4 THF:tert-butanol. The reaction mixture was stirred in ice for 0.5 hours and at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with pentane. The combined organic layer was washed with water. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and the solvent removed in vacuo to give an oil. Distillation gave 0.34 g (48% yield) of 1,3,9,11-dodecatetraene as established by proton and carbon-13 NMR and IR analysis.

Workup

  1. extractionextracted with pentane
  2. washThe combined organic layer was washed with water
  3. customThe organic layer was separated
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customto give an oil
  8. distillationDistillation

Sources & evidence

ORD record
ord-98c37596b1b944aca4c25eb66d020ffd
Source dataset
uspto-grants-1986_08
Patent number
US04604480

Reaction notes

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