Attempted novel preparation of dihydrocoumarin and coumarin; obtention of aryl acrylates and 3-chloropropionates

It has been found that, contrary to the published report, there is no noticeable reaction between phenol and methyl acrylate in the presence of aluminum chloride to produce phenyl acrylate (1) and dihydrocoumarin (2). Although products having the reported spectral data can be obtained by the reaction of phenol with acrylyl chloride, these products are actually phenyl acrylate and phenyl 3-chloropropionate (4), there being detected no dihydrocoumarin. This reaction has now been extended to several substituted phenols and some naphthols. Attempts at cyclization of phenyl acrylate, phenyl 3-chloropropionate, or their mixtures have been unsuccessful.