21574-35-6

Upstream product

• 95-48-7 ortho-cresol 
• 107-18-6 allyl alcohol 
• 4873-09-0 allyl tosylate 
• 936-72-1 allyl o-tolyl ether 
• 19689-33-9 6-allyl-6-methyl-cyclohexa-2,4-dien-1-one 

Downstream Products

• 98017-83-5 2-(4-Allyl-2-methyl-phenoxy)-propionic acid 
• 40793-86-0 4-(2-propenyl)-1-methoxy-2-methylbenzene 

Relevant academic research and scientific papers

Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates

The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.

Microwave-accelerated Claisen rearrangement in bicyclic imidazolium [b-3C-im][NTf2] ionic liquid

With microwaves, a chemically stable ionic liquid [b-3C-im][NTf2] recently developed in our laboratory was used as solvent and successfully applied to accelerate Claisen rearrangement reactions at high temperatures. In the presence of Lewis acid MgCl2, these thermal rearrangements could be achieved in similar reaction times but at lower temperature. For the microwaved reactions studied in this work, without scarifying isolated yields, the reaction times were significantly reduced from hours (by conventional heating) to ≤3 min. Our result also demonstrated that [b-3C-im][NTf2] ionic liquid was a useful solvent substitute and could be recycled multiple times for the studied rearrangement reaction at elevated temperatures.

Rhodium- and iridium-catalyzed allylation of electron-rich arenes with allyl tosylate

The allylation of electron-rich arenes with allyl tosylate proceeded at 0°C in the presence of [Rh(nbd)(CH3CN)2]PF 6. Various oxygenated arenes were allylated with high para-selectivity in almost all cases. Especially in t

Water-Accelerated Claisen Rearrangements

Allyl aryl ethers undergo accelerated Claisen and [1,3] rearrangements in the presence of a mixture of trialkylalanes and water or aluminoxanes. The ratio of ortho-, meta-, and pora-Claisen products depends to a large extent on the presence of water and to a much lesser extent on the nature of the alane.

CATALYSIS OF THE CYCLOHEXADIENONE-PHENOL REARRANGEMENT BY A LEWIS-ACIDIC CLAY SYSTEM

The Fe(3+)-doped acidic K10 clay accelerates greatly, by factors of 105-106, the title reaction.These rearrangements thus occur in a few minutes at room temperature, according to and pathways.