tert-Butanol → HCID 41971, compound

HRID 364249Notes

Reaction equation

HRID 364249 reaction equation
[C:1](O)([CH3:4])([CH3:3])C.C[C:7]([CH3:10])([O-])[CH3:8].[K+].[CH2:12]1[CH2:16]OC[CH2:13]1>O>[CH2:13]=[CH:12][CH:16]=[CH:8][CH2:7][CH2:10][CH2:3][CH2:1][CH3:4]

Participants

5

Reactant 3

HCID 6386tert-Butanol2×HCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 41971HCID 41971, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The latter compound (5.4 g) was dissolved in 20 mL of 1:9 THF:tert-butanol and added dropwise to an ice cold solution of potassium tert-butoxide (6.75 g) in 100 mL of 1:9 THF:tert-butanol. The reaction mixture was stirred in ice for 1 hour and at room temperature for 0.5 hours. The reaction mixture was diluted with water (200 mL) and extracted with pentane (2×75 mL). The combined organic layer was washed with water (4×150 mL). The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and the solvent removed in vacuo to give an oil. Distillation gave 1.79 g (72% yield) of a 2:1 mixture of (Z)- and (E)-1,3-nonadiene as established by NMR, IR and capillary GC analysis.

Workup

  1. extractionextracted with pentane (2×75 mL)
  2. washThe combined organic layer was washed with water (4×150 mL)
  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
  9. customgave

Sources & evidence

ORD record
ord-b1a936fb4a9b4ec69840d3989a314d2f
Source dataset
uspto-grants-1986_08
Patent number
US04604480

Reaction notes

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