83693-52-1

Upstream product

• 150-76-5 4-methoxy-phenol 
• 2344-80-1 Chloromethyltrimethylsilane 

Downstream Products

• 13391-32-7 2-ethyl-4-methoxy-phenol 
• 83693-59-8 4-methoxy-2-<2-(trimethylsilyl)ethyl>phenol 
• 150-76-5 4-methoxy-phenol 
• 1079438-07-5 N-methoxycarbonyl-2-(4-methoxyphenyloxymethyl)pyrrolidine 

Relevant academic research and scientific papers

Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents

A new neutral silicon-based traceless activation group (TAG) for visible-light photoredox-catalyzed hydroalkoxymethylation of alkenes is presented. This reaction involves in-situ-generated alkoxymethyl radical via single electron oxidation (SET) of α-TMS-substituted ethers, followed by subsequent conjugate addition to activated alkenes. Various functional groups were tolerated both under mild metal and metal-free conditions to provide good to excellent yields. Furthermore, the addition products were transformed to valuable synthetic building blocks, such as carboxylic acids,-butyrolactones, and complex aryl alkyl ethers.

Rearrangement and Cleavage of silanes by Organolithium Reagents: Conversion of Phenols into Benzylic Alcohols

The feasibility of converting phenols into their corresponding benzylic alcohols by means of novel Wittig rearrangement has been investigated.The method consists of (a) treating the phenol with (chloromethyl)trimethylsilane and base to produce the aryl (trimethylsilyl)methyl ether, (b) using sec- or n-BuLi in THF transform this ether into the α-(trimethylsilyl)benzylic alcohol, and (c) removing the silyl group with alcoholic KOH to yield the benzylic alcohol.With phenols, such as phenol itself, 2-naphthol, and 9-phenanthrol, benzylic alcohols were obtained in 50-80percent yields.Ring substituents of a nitro or methoxy type tend to favor α elimination in step b, at the expense of the Wittig rearrangement.The competitive nature of these latter two processes was examined as a function of substituents on the aryloxy groups or on the silicon, as well as a function of the lithium reagent and solvent employed.The independent synthesis and the thermal study of (phenoxymethyl)lithium demonstrated that in THF it undergoes an α elimination almost to the complete exclusion of any Wittig rearrangement.The relative importance of these two processes is discussed in terms of the locoselectivity of lithiation and an electron-transfer view of the Wittig aryl ether rearrangement.