Potassium Iodide → 2,5-Dihydrofuran

HRID 1250024Notes

Reaction equation

HRID 1250024 reaction equation
[I-].[K+].[CH3:3]/[C:4](/O[Al](O/C(/C)=C\C(C)=O)[O:11]/[C:12](/C)=[CH:13]\[C:14]([CH3:16])=O)=[CH:5]/[C:6](C)=[O:7].O1C(CC)=C1.I>[I-].[Zn+2].[I-].CN1CCCC1=O>[O:11]1[CH2:16][CH:14]=[CH:13][CH2:12]1.[CH:6](=[O:7])/[CH:5]=[CH:4]/[CH3:3]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 24841Hydrogen iodideHCID 10313053HCID 10313053, compound2×HCID 16683006HCID 16683006, compound

Product 2

HCID 155702,5-DihydrofuranYield 54%HCID 447466CrotonaldehydeYield 5%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 300 mL Fischer-Porter glass reactor were charged zinc iodide (3.0 g, 0.009 mol), potassium iodide (1.0 g, 0.006 mol), aluminum acetylacetonate (1.9 g, 0.006 mol), epoxybutene (30 g, 0.43 mol), hydrogen iodide (2.0 g, 0.009 mol), and N-methylpyrrolidone (120 g). The reactor was purged three times with nitrogen and was pressurized to 20 psig with nitrogen. The reactor was agitated by a magnetic stirrer and heated by an oil bath. The temperature was brought up to 120° C. and held at this temperature for 90 minutes. After cooling to room temperature, the reaction mixtures were analyzed by gas chromatography. GC indicated that all epoxybutene was consumed. Distillation of reaction mixtures afforded 2,5-dihydrofuran (16.3 g, 54% yield) and crotonaldehyde (1.5 g, 5%). Distillation under high vacuum afforded 10.2 grams of oligomer (34%).

Workup

  1. customThe reactor was purged three times with nitrogen
  2. temperatureheated by an oil bath
  3. customwas brought up to 120° C.
  4. customthe reaction mixtures
  5. customwas consumed
  6. distillationDistillation of reaction mixtures

Sources & evidence

ORD record
ord-29a55186d5314cf78f64f4ad08da191e
Source dataset
uspto-grants-2002_01
Patent number
US06335455B1

Reaction notes

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