19182-94-6

Upstream product

• 93981-82-9 2,4-dimethyl(allyloxy)benzene 
• 1879-09-0 2,4-dimethyl-6-tert-butylphenol 
• 4278-93-7 4,6-Dimethyl-6-allyl-cyclohexa-2,4-dien-1-on 
• 91-66-7 N,N-diethylaniline 

Downstream Products

• 1260370-69-1 (Y(2-allyl-4,6-dimethylphenolato)2(μ-2-allyl-4,6-dimethylphenolato))2 
• 1260370-68-0 (Sm(2-allyl-4,6-dimethylphenolato)2(μ-2-allyl-4,6-dimethylphenolato))2 
• 1260370-67-9 (La(2-allyl-4,6-dimethylphenolato)2(μ-2-allyl-4,6-dimethylphenolato))2 
• 1570067-65-0 C₁₃H₁₆O₃S 
• 126707-90-2 5,7-dimethyl-2-(phenylthiomethyl)-2,3-dihydrobenzofuran 
• 126708-09-6 2-<2-hydroxy-3-(phenylthio)propyl>-4,6-dimethylphenol 
• 126708-19-8 2-<3-hydroxy-2-(phenylthio)propyl>-4,6-dimethylphenol 
• 860734-43-6 2-allyl-4,6-dimethyl-anisole 
• 65001-65-2 2,4-Dimethyl-6-cis-propenyl-phenol 
• 65001-64-1 2,4-Dimethyl-6-trans-propenyl-phenol 
• 100971-61-7 allyl-(2,4-dimethyl-6-trans-propenyl-phenyl)-ether 
• 65001-66-3 2,4-dimethyl-6-propenyl-anisole 
• 104175-17-9 1-(2-Oxy-3.5-dimethyl-phenyl)-propen-⁽¹⁾ 

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.

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.

Organoaluminum-Promoted Rearrangement of Allyl Phenyl Ethers

The Claisen rearrangement of allyl phenyl ethers with exceptionally bulky, oxygenophilic methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (reagent A) is found to exhibit an unusual behavior not observable in the ordinary thermal and Lewis acid-induc

Synthesis of methyl 2,3-dihydro-2-benzofurancarboxylates from o-allylphenols via 2-(phenylthiomethyl)-2,3-dihydrobenzofurans

A method for synthesizing methyl 2,3-dihydro-2-benzofurancarboxylates rom o-allylphenols is described.The reaction of 6allyl-2,3-dichlorophenol (3) with benzenesulfenyl chloride (PhSCl) in acetonitrile gave a mixture of PhSCl -adducts, which was heated in aqueous acetonitrile then with sodium bicarbonate to obtain 6,7-dichloro-2-(phenylmethyl)-2,3-dihydrobenzofuran (6). α-Dichlorination of the phenylthiomethyl group of 6 and subsequent methanolysis gave the methyl ester 5 in high yield.The generality of this synthetic method was examined by the conversion of o-allylphenols 11 having various substituents on the benzene ring into the corresponding methyl ester 23.Cyclization of 11 to sulfides 12 could be achived similerly to the case of 3.However, in the subsequent conversions of 12 to 23, selective α-dichlorination followed by methanolysis could be achived only with 12 substituted with an electron-withdrawing group such as a chloro or nitro group.Keywords - oallylphenils; methyl 2,3-dihydro-2-benzofurancarboxylate; 2-(phenylthiomethyl)-2,3-dihydrobenzofuran; benzenesulfenyl chloride; α-chlorination; methanolysis.

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.