Since acetone is converted into its enol form under acidic conditions, could it participate in Fischer esterification to form an enol acetate? For example, would refluxing acetone, p-TSA, and acetic acid form the unsaturated ester?

Reaction scheme

  • $\begingroup$ My suspicion is no, although apparently you can transesterify by refluxing acetone with TsOH + allyl acetate (JOC 2012, 77, 10347) $\endgroup$ – orthocresol Apr 16 '18 at 23:50

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