41321-75-9Relevant articles and documents
Reaction of 4-Haloacetoacetate with Phenols in the Presence of Aluminium Chloride
Kimura, Hitoshi,Sato, Hirotoshi,Tsuchiya, Chizuko,Chiba, Takuo,Kato, Tetsuzo
, p. 552 - 558 (2007/10/02)
Reaction of ethyl 4-bromoacetoacetate (1) with phenol in the presence of aluminium chloride gave ethyl 4-bromo-3-hydroxy-3-(2-hydroxyphenyl)butyrate (3a), which can be regarded as an intermediate of the Pechmann reaction.Similar reaction of ethyl 4-chloroacetoacetate (7) with phenol in the presence of aluminium chloride gave the 4-chloro derivative 8a.Compound 3a was treated with either hydrogen chloride in ethanol or triethylamine followed by treatment with p-toluenesulfonic acid to give 4-bromomethylcoumarin (4a) or ethyl 3-benzofuranacetate (6a), respectively.Similarly, reactions of phenol derivatives 2 with 1 gave the corresponding 3-hydroxybutyrates 3, which were transformed to the coumarins 4 and the 3-benzofuranacetates 6.