β-AROYL-α- AND -β-ARYLPROPIONIC ACIDS: PART I. THEIR PREPARATION AND LACTONIZATION

Abstract

Bromobenzene reacts with phenyl- and p-methoxyphenyl-succinic anhydride in the presence of anhydrous aluminum chloride to give a mixture of β-p-bromobenzoyl-α- and -β-phenyl-propionic acid, and a mixture of β-p-bromobenzoyl-α- and -β-p-hydroxyphenylpropionic acid, respectively.Similarly, iodobenzene reacts with the same anhydrides to give a mixture of β-p-iodobenzoyl-α- and -β-phenylpropionic acid and β-benzoyl-α- and -β-phenylpropionic acid, and a mixture of β-benzoyl- and β-p-iodobenzoyl-α-p-methoxyphenylpropionic acid, respectively.Phenyl- and diphenyl-succinic anhydride are cyclized by aluminum chloride to 1-ketoindane- and 1-keto-2-phenylindane-3-carboxylic acid, respectively.The above keto acids are converted by boiling acetic anhydride into β,γ-unsaturated γ-lactones.