75501-56-3

Upstream product

• 59701-65-4 4-(2,5-dihydroxyphenyl)-4-oxobutanoic acid 
• 108-24-7 acetic anhydride 
• 123-31-9 hydroquinone 
• 34428-26-7 4-Hydroxyphenyl Hydrogen Succinate 
• 127275-13-2 Methyl 4-(2,5-Dihydroxyphenyl)-4-oxobutanoate 
• 1084-74-8 3-(2,5-dimethoxybenzoyl)propionic acid 

Downstream Products

• 79238-15-6 2',5'-diacetoxyphenyl vinyl ketone 
• 79238-21-4 6-acetoxy-3-carbethoxymethyl-2-methyl chromone 

Relevant academic research and scientific papers

Photochemical Versus Aluminium Chloride-Catalyzed Fries Rearrangement of Aryl Hydrogen Succinates. Synthesis of 2(3H)-Furanones

The photochemical and aluminium chloride-catalyzed Fries rearrangement of a series of aryl hydrogen succinates 3 a-f to the corresponding 4-oxoacids 1 a-f are compared.Both approaches are complementary: the photochemical process is more general and becomes the method of choice for the succinoylation of phenols supporting alkoxy or hydroxy substituents, while the classical rearrangement is superior in the presence of alkyl or halogen substituents.These results are applied to the preparation of the 2(3H)-furanones 2 a-f. - Keywords: Fries rearrangement; Photo-Fries rearrangement; Aryl hydrogen succinates; 4-Oxoacids; 2(3H)-Furanones.

PHOTOCHEMISTRY OF 5-ARYL-2(3H)-FURANONES. A NEW ROUTE TO THE SYNTHESIS OF CHROMONES

The photochemistry of 5-phenyl-, 5-(2',5'-dimethoxyphenyl)-, 5-(2'-acetoxy-5'-methoxyphenyl)- and 5-(2',5'-diacetoxyphenyl)-2(3H)-furanone (1a-d) has been investigated.Compound 1a yields pheny vinyl ketone as expected.Similarly, 1b affords the corresponding aryl vinyl ketone but, in this case, photodimerization also occurs.Irradiation of the two o-acetoxyaryl furanones 1c and 1d gives rise to the formation of chromones as the main products.This interesting result can be accounted for in terms of a photochemical opening of the lactonic ring followed by radical addition to the acetoxy group.

Indirect Hidroquinone Succinoylation via a Photo-Fries Rearrangement. Application to the Synthesis of Enol Lactones

A photo-Fries rearrangement of hydroquinone succinates is the key step that allows the preparation of some γ-aryl enol lactones by dehydration of the corresponding aroyl propinoic acids.