156147-58-9

Upstream product

• 127866-65-3 5-[(4-methoxybenzyl)sulfanyl]-1-phenyl-1H-tetrazole 
• 108-93-0 cyclohexanol 
• 108-94-1 cyclohexanone 
• 105-13-5 4-Methoxybenzyl alcohol 
• 824-94-2 p-methoxybenzyl chloride 
• 866124-70-1 p-methoxybenzyloxydiphenylphosphine 
• 180259-48-7 1-methoxy-4-((pent-4-en-1-yloxy)methyl)benzene 

Downstream Products

• 108-93-0 cyclohexanol 
• 622-45-7 cyclohexyl acetate 
• 104-21-2 p-methoxybenzyl acetate 

Relevant academic research and scientific papers

Direct and efficient synthesis of unsymmetrical ethers from alcohols catalyzed by Fe(HSO4)3 under solvent-free conditions

Highly efficient Fe(HSO4)3 catalyzed etherification of primary, secondary and tertiary benzylic alcohols with primary and secondary aliphatic alcohols is reported. The reaction affords unsymmetrical benzyl ethers in good to excellent yields under solvent-free conditions.

Sulfated tungstate as hydroxyl group activator for preparation of benzyl, including p-methoxybenzyl ethers of alcohols and phenols

Sulfated tungstate was found to be an effective heterogeneous and reusable catalyst for hydroxy group activation–mediated preparation of benzylic ethers including p-methoxybenzylic ethers of a wide range of alcohols and phenols under mild reaction conditions.

Chemoselective formation of unsymmetrically substituted ethers from catalytic reductive coupling of aldehydes and ketones with alcohols in aqueous solution

A well-defined cationic Ru-H complex catalyzes reductive etherification of aldehydes and ketones with alcohols. The catalytic method employs environmentally benign water as the solvent and cheaply available molecular hydrogen as the reducing agent to afford unsymmetrical ethers in a highly chemoselective manner.

Gold(I)-catalyzed synthesis of unsymmetrical ethers using alcohols as alkylating reagents

A microwave-irradiated alcohol-protecting strategy based on gold catalysis utilizing benzyl alcohol, tert-butyl alcohol and triphenylmethanol as alkylating reagents has been developed. This protecting strategy has wide functional group tolerance with satisfactory yields for the majority of the selected alcohols. The mechanism of this transformation was probed with oxygen-18 isotope labelled alcohols assisted by GC-MS techniques and chemical kinetic experiments. This strategy provides an efficient, straightforward and alternative approach to the preparation of benzyl, tert-butyl and trityl ethers in organic synthesis.

Benzylation of hydroxy groups with tertiary amine as a base

The benzylation of hydroxy groups in the presence of tertiary amines is described. A mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields in the presence of diisopropylethylamine. The importance of solventless conditions was observed. The reaction showed high tolerance to many functional groups including benzoate, even at a reaction temperature of 150 °C. Sodium iodide was found to be an efficient catalyst to accelerate the reaction.

A simple and an efficient indium trichloride catalyzed benzyl etherification

An efficient method has been developed for the synthesis of benzyl ethers of alkyl, allyl and propargyl alchols by simple, direct coupling of alcohols in the presence of catalytic amount of L1C13 under solvent-free condition.

A mild method for the protection of alcohols using a para-methoxybenzylthio tetrazole (PMB-ST) under dual acid-base activation

With a view to expand the repertoire of chemoselective methods applicable to sensitive and multifunctional substrates, the p-methoxybenzylation of alcohols under essentially neutral conditions is reported. This was achieved by the silver triflate (AgOTf) activation of 5-(p-methoxybenzylthio)-1-phenyl-1H-tetrazole (PMB-ST) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP).

Efficient methods for the preparation of alkyl-aryl and symmetrical or unsymmetrical dialkyl ethers between alcohols and phenols or two alcohols by oxidation-reduction condensation

Oxidation-reduction condensation via alkoxydiphenylphosphines (diphenylphosphinite esters) (1), generated in situ from chlorodiphenylphosphine (2) and alcohols, 2,6-dimethyl-1,4-benzoquinone (3), and phenols proceeds smoothly to afford alkyl-aryl ethers in good to high yields under neutral conditions. In a similar fashion, a new and efficient method for the preparation of symmetrical or unsymmetrical dialkyl ethers in good to high yields is established via tetrafluoro-1,4-benzoquinone (fluoranil) (4), alcohols, and 1 formed in situ from nBuLi-treated alcohols and 2. This method is applicable also to the etherification of chiral secondary or tertiary alcohols with retention or inversion of configurations. The inverted ethers are afforded by treating chiral alkoxydiphenylphosphines and achiral alcohols, while the reaction of achiral alkoxydiphenylphosphines and chiral alcohols forms retained ethers.

A Convenient Method for the Preparation of Symmetrical or Unsymmetrical Ethers by the Coupling of Two Alcohols via a New Type of Oxidation-reduction Condensation Using Tetrafluoro-1,4-benzoquinone

A new type of oxidation-reduction condensation by using tetrafluoro-1,4-benzoquinone (fluoranil), alcohols and alkoxydiphenylphosphines, in situ formed from nBuLi-treated alcohols and chlorodiphenylphosphine, proceeded smoothly to afford the corresponding symmetrical or unsymmetrical ethers in good to high yields.

A mild method for generation of p-methoxybenzyl cation through NIS- mediated activation of p-methoxybenzyl 4-pentenyl ether

A mild and facile method for generation of p-methoxybenzyl cation through NIS-mediated activation of p-methoxybenzyl 4-pentenyl ether was achieved. Under the present activation conditions, various alcohols were convened to the corresponding p-methoxybenzyl ethers. A scope and limitation of the present p-methoxybenzylation reaction was also investigated.