220884-51-5

Basic information

• Product Name: methyl 4-acetoxy-4-methoxy-3-oxocyclohexa-1,5-dienecarboxylate
• Synonyms: methyl 4-acetoxy-4-methoxy-3-oxocyclohexa-1,5-dienecarboxylate
• CAS NO: 220884-51-5
• Molecular Weight: 240.213
• Mol File: 220884-51-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 4-acetoxy-4-methoxy-3-oxocyclohexa-1,5-dienecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-acetoxy-4-methoxy-3-oxocyclohexa-1,5-dienecarboxylate(220884-51-5)
• EPA Substance Registry System: methyl 4-acetoxy-4-methoxy-3-oxocyclohexa-1,5-dienecarboxylate(220884-51-5)

Safety Data

• Hazardous Substances Data: 220884-51-5(Hazardous Substances Data)

Upstream product

• 645-08-9 Isovanillic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 6702-50-7 3-hydroxy-4-methoxybenzoate 

Downstream Products

• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 170124-07-9 methyl 4-methoxy-3-phenoxybenzoate 

Relevant articles and documents

Orthoquinone monoketal chemistry. Experimental and density functional theory studies on orthoquinol acetate rearrangements

The non-dimerizing orthoquinone monoketal, 6-acetoxy-6-methoxy-3- methoxycarbonylcyclohexa-2,4-dienone, conveniently prepared from oxidative acetoxylation of its parent phenol with PhI(OAc)2 in CH2Cl2-AcOH (3:1), cleanly undergoes 1,3-acetoxy migrations in the presence of silica gel at room temperature to furnish a 60:40 product mixture conceivably derived from [3,5] and [3,3] sigmatropic rearrangements. Density functional theory calculations indicate that the [3,5] shift is pseudopericyclic, has a remarkably low activation energy of 20.1 kcal/mol, and is favored by 5.4 kcal/mol over the pericyclic [3,3] shift, in qualitative agreement with the experimental observations.

2-Alkoxyarenol-derived orthoquinols in carbon-oxygen, carbon-nitrogen and carbon-carbon bond-forming reactions

Silylated oxygen- and nitrogen-tethered orthoquinol acetates, generated by phenyliodine(III) diacetoxy-mediated oxidative acetoxylation of 2-alkoxyphenols in CH2Cl2 can be used to furnish regioselectively benzannulated heterocycles. Oxidative activation of 2-alkoxynaphthols with non-nucleophilic phenyliodine(III) bis(trifluoroacetoxy) in the presence of carbon nucleophiles, including oxidation sensitive silyl enol ethers, constitute a potentially valuable route to naturally occurring vicinally oxygenated benz[a]anthracene motifs.