31910-25-5

Upstream product

• 108-24-7 acetic anhydride 
• 136-90-3 4-methoxy-3-methylaniline 
• 16375-90-9 4-acetamido-2-methylphenol 
• 77-78-1 dimethyl sulfate 
• 89345-80-2 4-O-Methyl-4-methyl-p-benzoquinol N-acetylimine 
• 27451-21-4 N-hydroxy-N-(p-tolyl)acetamide 
• 89345-78-8 C₁₀H₁₃NO₄S 
• 50741-92-9 2-methyl-4-nitroanisole 
• 2835-96-3 4-amino-2-methylphenol 
• 67-56-1 methanol 
• 537-92-8 3-Methylacetanilide 
• 74-88-4 methyl iodide 
• 6971-38-6 p-nitroso-o-cresol 
• 95-48-7 ortho-cresol 

Downstream Products

• 344794-49-6 2-chloro-4-methoxy-5-methyl-aniline 
• 518990-51-7 acetic acid-(4-methoxy-5-methyl-2-nitro-anilide) 
• 136-90-3 4-methoxy-3-methylaniline 
• 13120-77-9 2-methyl-5-nitroanisole 
• 55730-09-1 4-methoxy-5-methyl-2-nitroaniline 
• 1295585-45-3 2-(4-methoxy-3-methylphenyl)hydrazono-5-methylcyclohexanone 
• 1185297-84-0 4-methoxy-3-methylaniline hydrochloride 

Relevant academic research and scientific papers

Selective, Catalytic, and Metal-Free Coupling of Electron-Rich Phenols and Anilides Using Molecular Oxygen as Terminal Oxidant

Selective oxidative homo- and cross-coupling of electron-rich phenols and anilides was developed using nitrosonium tetrafluoroborate as a catalyst. Oxidative coupling of phenols revealed unusual selectivities, which translated into the unprecedented synthesis of inverse Pummerer-type ketones. Mechanistic studies suggest that oxidative coupling of phenols and anilides shares a common pathway via homolytical heteroatom-hydrogen bond cleavage. Nitrosonium salt catalysis was applied for cross-dehydrogenative coupling initiated by generation of heteroatom-centered radicals.

A novel CAN-SiO2-mediated one-pot oxidation of 1-keto-1,2,3,4-tetrahydrocarbazoles to carbazoloquinones: Efficient syntheses of murrayaquinone A and koeniginequinone A

One-pot oxidations of substituted 1-keto-1,2,3,4-tetrahydrocarbazoles (1) to carbazole-1,4-quinones (2) are efficiently carried out by CAN-SiO 2-mediated reaction. This generalized protocol was successfully extended to the synthesis of two naturally occurring carbazoloquinones: murrayaquinone A (2b) and koeniginequinone A (2g). A plausible mechanism for this novel reaction involves formation of a 9-hydroxy-2,3,4,9-tetrahydro-1H- carbazole-1-one followed by rearrangement to 1-hydroxycarbazole derivatives, which are further oxidized by cerium (IV) to carbazoloquinones.

Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate)

Treatment of various anilides with 1.5 equiv. of phenyliodine bis(trifluoroacetate) (PIFA) and 1.0 equiv. of BF3·OEt 2 in AcOH at room temperature afforded the corresponding para-acetoxylated products with high regioselectivity. In addition, this reaction could be expanded to the etherification of anilides. In the presence of 2.0 equiv. of PIFA and 2.0 equiv. of BF3·OEt2, the reaction of anilides with alcohols provided the corresponding para-etherified products in good yields. The Royal Society of Chemistry 2011.