tert-Butanol → 1-Ethenylcyclohept-1-ene

HRID 364246Notes

Reaction equation

HRID 364246 reaction equation
[C:1](O)([CH3:4])([CH3:3])[CH3:2].[CH3:6]C(C)([O-])C.[K+].[CH2:12]1[CH2:16]O[CH2:14][CH2:13]1>O>[CH:2]([C:1]1[CH2:4][CH2:16][CH2:12][CH2:13][CH2:14][CH:3]=1)=[CH2:6]

Participants

5

Reactant 3

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

Product 1

HCID 126820621-Ethenylcyclohept-1-eneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The latter compound (6.7 g) was dissolved in 40 mL of 1:9 THF:tert-butanol and added dropwise to an ice cold solution of potassium tert-butoxide (8.44 g) in 100 mL of 1:9 THF:tert-butanol. The reaction mixture was stirred in ice for 0.5 hours and at room temperature for 0.5 hours. The reaction mixture was diluted with water (200 mL) and extracted with pentane (2×50 mL). The combined organic layer was washed with water (7×150 mL). organic layer was separated, dried with anhydrous magnesium sulfate, filtered and the solvent removed at atmospheric pressure using a Vigreaux column to give a liquid. Distillation gave 2.6 g (85% yield) of 1-vinyl cycloheptene as established by NMR and IR analyis.

Workup

  1. extractionextracted with pentane (2×50 mL)
  2. washThe combined organic layer was washed with water (7×150 mL)
  3. customorganic layer was separated
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed at atmospheric pressure
  7. customto give a liquid
  8. distillationDistillation

Sources & evidence

ORD record
ord-5579cbcf3cd44a0fb6195f59285a635f
Source dataset
uspto-grants-1986_08
Patent number
US04604480

Reaction notes

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