73396-43-7

Basic information

• Product Name: Phenol, pentamethyl-, acetate
• CAS NO: 73396-43-7
• Molecular Formula: C13H18O2
• Molecular Weight: 206.285
• Mol File: 73396-43-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Phenol, pentamethyl-, acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, pentamethyl-, acetate(73396-43-7)
• EPA Substance Registry System: Phenol, pentamethyl-, acetate(73396-43-7)

Safety Data

• Hazardous Substances Data: 73396-43-7(Hazardous Substances Data)

Upstream product

• 700-12-9 pentamethylbenzene, 
• 64-19-7 acetic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 

Relevant articles and documents

Gold-catalyzed oxidative acyloxylation of arenes

A variety of nonactivated hindered aromatic rings are acyloxylated (22 examples, up to 83% yield) in the presence of PPh3AuCl as the catalyst and di(acetoxy)iodobenzene as the oxidant. The reaction proceeds at 110 °C in an acid media and allows the formation of both hindered acetoxy and acyloxy derivatives. This methodology nicely complements the Pd-catalyzed arene acyloxylation reaction, which is not operating on hindered substrates and allows the Au-catalyzed unprecedented acyloxylation reaction of arenes, implying various carboxylic acids.

Photorearrangements of Epoxy Ketones. Epoxides of Hexamethylbicyclohepta-2,5-dienone, a Valence Tautomer of Hexamethyltropone

The double bond in the four-membered ring of hexamethylbicyclohepta-3,6-dien-2-one (1) is selectively oxidized by m-chloroperbenzoic acid, whereas the enone double bond is selectively epoxidized by alkaline hydrogen peroxide to give 2 and 3, respectively.In each case, a single stereoisomer is formed.The exo stereochemistry of the epoxides was deduced from X-ray structures on diepoxides 4 and 5 obtained by further epoxidation of 2 and 3.Irradiation of 2 gives pentamethylphenol (6) and ketene; if 2 is labeled at the C4 methyl with deuterium, the resulting 6 is labeled para to the hydroxyl group.A novel rearrangement of the four-membered ring to give a 7-norbornenyl-type intermediate is suggested to rationalize the labeling result.Irradiation of 3 gives, in addition to minor amounts of pentamethylphenol and its acetate, a tetracyclic product formulated as 10, which rearranges thermally to 1-acetylpentamethylcyclopentadiene (12).A mechanism involving photochemical C-C bond cleavage of the epoxide ring in 3 is suggested to account for the results.