548464-35-3

Upstream product

• 2216-51-5 (-)-menthol 
• 105-13-5 4-Methoxybenzyl alcohol 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 2746-25-0 p-Methoxybenzyl bromide 
• 937184-70-8 2-(4-methoxybenzyloxy)-4-methylquinoline 
• 333-27-7 methyl trifluoromethanesulfonate 
• 1450734-54-9 4-methoxybenzyl N-phenyl-2,2,2-trifluoroacetimidate 
• 100867-01-4 (4-methoxybenzyl)(4-nitrophenyl)sulfane 
• 123-11-5 4-methoxy-benzaldehyde 
• 824-94-2 p-methoxybenzyl chloride 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 775356-24-6 4-(2-isopropyl-5-methyl-cyclohexyloxymethyl)-phenol 
• 866124-70-1 p-methoxybenzyloxydiphenylphosphine 

Downstream Products

• 54879-64-0 N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide 
• 2216-51-5 (-)-menthol 

Relevant academic research and scientific papers

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Oxidative Deprotection of p-Methoxybenzyl Ethers via Metal-Free Photoredox Catalysis

An efficient and greener deprotection method for p-methoxybenzyl (PMB) ethers using a metal-free visible light photoredox catalyst and air and ammonium persulfate as the terminal oxidants is presented. Various functional groups and protecting groups were tolerated in the developed method to achieve good to excellent yields in short reaction times. Significantly, the developed method was compatible with PMB ethers derived from primary, secondary, and tertiary alcohols and a gram-scale reaction. Mechanistic studies support a proposed reaction mechanism that involves single electron oxidation of the PMB ether.

Simple and rapid p-methoxybenzylation of hydroxy and amide groups at room temperature by NaOt-Bu and DMSO

The p-methoxybenzylation of hydroxy and amide groups by p-methoxybenzyl chloride utilizing NaOt-Bu in DMSO is described. p-Methoxybenzylation of sterically hindered menthol using NaOt-Bu in DMSO proceeded faster than the commonly used methods which use Na

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.

Photoredox removal of p-methoxybenzyl ether protecting group with hydrogen peroxide as terminal oxidant

We report a mild protocol for removal of the p-methoxybenzyl ether protecting group under acidic conditions with eosin Y combined with LEDs as a photoredox catalysis system and hydrogen peroxide as the terminal oxidant. This protocol is compatible with ethers derived from primary, secondary, and tertiary alcohols, as well as with various functional groups. The protocol showed unusual selectivity for a tertiary ether over a primary ether. The scale up to gram scale is also explored and identical reactivity is observed.

Facile and selective deprotection of PMB ethers and esters using oxalyl chloride

Oxalyl chloride, (0.5 equiv) was found to cleave the PMB group from alkyl, aryl PMB ethers, and esters to give corresponding alcohol and acid in good yields. This method offers simple and efficient protocol for the selective deprotection of PMB ether and ester in DCE at ambient temperature.

A convenient approach for the deprotection and scavenging of the PMB group using POCl3

A convenient and high yielding approach for the deprotection and scavenging of the p-methoxybenzyl (PMB) group in PMB ethers and PMB esters was developed using POCl3 as the reagent. 4-Methoxybenzyl chloride, a starting material used for the preparation of PMB ethers and esters was regenerated in the deprotection step. This mild and selective procedure tolerates several acid sensitive functional groups. The Royal Society of Chemistry 2013.

P-Methoxybenzyl-N-phenyl-2,2,2-trifluoroacetimidate: A versatile reagent for mild acid catalyzed etherification

PMB-NPTFA 1a is a new month bench stable and powerful reagent for the formation of PMB ethers. Several alcohols were protected in high yields and short reaction times, using low reagent loading and small catalytic amounts of Bi(OTf)3. The mild

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.

Silver(I)-Catalyzed deprotection of p -methoxybenzyl ethers: A mild and chemoselective method

The p-methoxybenzyl protecting group (PMB) on various alcohols and an acid was efficiently and selectively cleaved by the action of a catalytic amount of silver(I) hexafluoroantimonate combined with 0.5 equiv of 1,3,5- trimethoxybenzene in dichloromethane at 40 °C.