189366-70-9

Upstream product

• 148675-55-2 1-(4-methoxybenzyloxy)-2-(2-propyl)-2-propene 
• 203583-38-4 3-(4-ethoxybenzyloxy)-2-methyl-1-propene 
• 824-94-2 p-methoxybenzyl chloride 
• 26903-66-2 2-isopropylallyl alcohol 
• 189366-67-4 3-(4-methoxybenzyloxy)-2-methyl-1-propene 
• 203633-74-3 3-(4-ethoxybenzyloxy)-2-(2-propyl)-1-propene 

Relevant academic research and scientific papers

Rearrangement of p-methoxybenzyl-protected allylic alcohols to aldehydes

Allyl p-methoxybenzyl ethers undergo an acid-catalysed 1,4-rearrangement to give p-methoxyphenylbutyraldehyde derivatives, which can be ring-closed to give substituted naphthalene derivatives.

Mechanistic aspects of the zeolite β induced rearrangement of alkoxybenzyl allyl ethers to aldehydes and ketones

The mechanism for the novel zeolite β catalyzed rearrangement of alkoxybenzyl allyl ethers to aldehydes and ketones has been investigated by use of cross reactions and deuterium labeling. The reaction is mainly intramolecular and may be described as a nucleophilic attack of the double bond on the electrophilic benzylic carbon of the ether-Lewis acid complex, followed by a 1,2-hydride (or alkyl) migration. Acta Chemica Scandinavica 1998.

Zeolite β induced rearrangement of alkoxybenzyl allyl ethers to aldehydes and ketones. Part IV. Investigation of the reaction conditions

The reaction conditions for the rearrangement of p-methoxybenzyl allyl ether 1 have been investigated with respect to catalysts and solvents. Zeolite β was the best catalyst but zeolite Y and mordenite were also effective. The Lewis acids BF3·OEt2, (iPrO)2TiCl2 and AlMe2Cl induced the rearrangment but were considerably less efficient than the solid catalysts. Protic acids were not very useful owing to the formation of too many products. Among the solvents tested dichloromethane and 1,1,2-trichloroethane were the most useful even though the rearrangement took place in several other solvents. Interestingly, 1 rearranged spontaneously on dissolution in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFP). Acta Chemica Scandinavica 1998.

Zeolite β-Induced Rearrangement of Alkoxybenzyl Allyl Ethers to Aldehydes and Ketones. 5.1 Variation of the Allylic Moiety

Allylic PMB ethers rearranged in the presence of zeolite β to form 4-arylbutanals or 5-arylpentanones depending on the substituent pattern of the allylic moiety. Best results were obtained with substrates carrying simple substituents in the allylic 2-posi