The Perkin condensation is an aldol-type condensation in which an aromatic aldehyde

Chapter 19, Problem 19.55

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The Perkin condensation is an aldol-type condensation in which an aromatic aldehyde (ArCHO) reacts with a carboxylic acid anhydride, (RCH2CO)2O, to give an a,b-unsaturated acid (ArCHCRCO2H). The catalyst that is usually employed is the potassium salt of the carboxylic acid (RCH2CO2K). (a) Outline the Perkin condensation that takes place when benzaldehyde reacts with propanoic anhydride in the presence of potassium propanoate. (b) How would you use a Perkin condensation to prepare p-chlorocinnamic acid, p-ClC6H4CHCHCO2H?

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