Isopropenyl acetate explained

Isopropenyl acetate is an organic compound, which is the acetate ester of the enol tautomer of acetone. This colorless liquid is significant commercially as the principal precursor to acetylacetone. In organic synthesis, it is used to prepare enol acetates of ketones and acetonides from diols.[1]

Preparation

Isopropenyl acetate is prepared by treating acetone with ketene. Upon heating over a metal surface, isopropenyl acetate rearranges to acetylacetone.[2]

Reactions

Isopropenyl acetate is used to prepare other isopropenyl ethers.[3]

Isopropenyl acetate reacts with ketones to give new enol acetates:

References

  1. Encyclopedia: Isopropenyl Acetate. Michael A.. Walters. Melissa D.. Lee. Encyclopedia of Reagents for Organic Synthesis. 2001. 10.1002/047084289X.ri077. 0471936235 .
  2. Encyclopedia: Ullmann's Encyclopedia of Industrial Chemistry. Weinheim . Wiley-VCH. Hardo. Siegel. Manfred. Eggersdorfer. Ketones. 10.1002/14356007.a15_077. 2002. 9783527306732 .
  3. Org. Synth.. 2012. 89. 307–310. 10.15227/orgsyn.089.0307. Discussion Addendum for: Iridium-catalyzed Synthesis of Vinyl Ethers from Alcohols and Vinyl Acetate. Yasushi. Obora. Yasutaka. Ishii.

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