2626-17-7Relevant academic research and scientific papers
A facile preparation of methoxymethyl ethers of primary and secondary alcohols with dimethoxymethane catalysed by expansive graphite
Jin, Tong-Shou,Li, Tong-Shuang,Gao, Yong-Tao
, p. 837 - 841 (1998)
An easy preparation of methoxymethyl ethers of primary and secondary alcohols with dimethoxymethane has been carried out in excellent yield under catalysis of expansive graphite.
Expanded substrate scope and improved reactivity of ether-forming cross-coupling reactions of organotrifluoroborates and acetals
Vo, Cam-Van T.,Mitchell, T. Andrew,Bode, Jeffrey W.
supporting information; experimental part, p. 14082 - 14089 (2011/10/12)
Mixed acetals and organotrifluoroborates undergo BF3· OEt2-promoted cross-couplings to give dialkyl ethers under simple, mild conditions. A survey of reaction partners identified a hydroxamate leaving group that improves the regioselectivity and product yield in the BF 3·OEt2-promoted coupling reaction of mixed acetals and potassium alkynyl-, alkenyl-, aryl- and heteroaryltrifluoroborates to access substituted dialkyl ethers. This leaving group enables the reaction to proceed rapidly under mild conditions (0 °C, 5-60 min) and permits reactions with electron-deficient potassium aryltrifluoroborates that are less reactive with other acetal substrates. A study of the reaction mechanism and characterization of key intermediates by NMR spectroscopy and X-ray crystallography identified a role for the hydroxamate moiety as a reversible leaving group that serves to stabilize the key oxocarbenium intermediate and the need for a slight excess of organodifluoroborane to serve as a catalyst. A secondary role for the boron nucleophile as an activating ligand was also considered. These studies provide the basis for a general class of reagents that lead to dialkyl ethers by a simple, predictable cross-coupling reaction.
Efficient and selective formation of mixed acetals by Nafion-H SAC-13 silica nanocomposite solid acid catalyst
Ledneczki, Istvan,Molnar, Arpad
, p. 3683 - 3690 (2007/10/03)
Various types of hydroxy compounds can readily be converted to the corresponding mixed acetals with dialkoxymethanes in the presence of SAC-13 solid superacid. The transformation is almost instantaneous, product acetals are isolated in good to excellent yields, and the catalyst can be reused with minor loss of activity. Comparative studies were also carried out with p-toluenesulfonic acid and BF3·OEt2.
Scandium trifluoromethanesulfonate as a recyclable catalyst for efficient methoxymethylation of alcohols
Karimi, Babak,Ma'mani, Leyla
, p. 6051 - 6053 (2007/10/03)
Scandium triflate [Sc(OTf)3] has been found to be a recyclable catalyst for mild highly efficient methoxymethylation of a variety of alcohols using formaldehyde dimethyl acetal (FDMA).
TiO2/SO42-, an efficient catalyst for the methoxymethylation of alcohols
Jin, Tong-Shou,Guo, Jun-Jie,Yin, Ya-Hui,Zhang, Su-Ling,Li, Tong-Shuang
, p. 188 - 189 (2007/10/03)
Methoxymethylation of primary and secondary alcohols with dimethoxymethane has afforded the corresponding methoxymethyl ethers in good to high yields in the presence of TiO2/SO42- solid superacid.
Envirocat EPZGR Catalysed Methoxymethylation of Alcohols
Bandgar,Hajare,Wadgaonkar
, p. 90 - 91 (2007/10/03)
Envirocat EPZGR is an efficient reusable heterogenous catalyst for the methoxymethylation of alcohols. The isolation of pure products by simple filtration and evaporation is an important feature of this method.
Montmorillonite catalysed methoxymethylation of alcohols
Kantam, M. Lakshmi,Santhi, P. Lakshmi
, p. 260 - 261 (2007/10/03)
Montmorillonite is an effective heterogeneous catalyst for the methoxymethylation of alcohols.
Sulfated zirconia as an efficient catalyst for the methoxymethylation of alcohols
Sarkar, Anjana
, p. 862 - 863 (2007/10/03)
Primary and secondary alcohols react with dimethoxymethane in the presence of a catalytic amount of sulfated zirconia to afford the corresponding methoxy methyl ethers (MOM ether) in good to high yields.
MILD CLEAVAGE OF METHOXYMETHYL (MOM) ESTERS WITH TRIMETHYLSILYLBROMIDE
Hanessian, Stephen,Delorme, Daniel,Dufresne, Yves
, p. 2515 - 2518 (2007/10/02)
Trimethylsilyl bromide is an effective reagent for the deprotection of methoxymethyl ethers under mild conditions.
