Benzene,1,1'-[oxybis(methylene)]bis[4-methoxy-

Base Information

• Chemical Name: Benzene,1,1'-[oxybis(methylene)]bis[4-methoxy-
• CAS No.: 5405-95-8
• Molecular Formula: C16H18 O3
• Molecular Weight: 258.317
• Mol file: 5405-95-8.mol

Synonyms:Ether,bis(p-methoxybenzyl) (7CI,8CI); Bis(4-methoxybenzyl)ether; Bis(p-methoxybenzyl)ether; NSC 406876; NSC 5258; Toluene, a,a'-oxybis[p-methoxy-

Chemical Property of Benzene,1,1'-[oxybis(methylene)]bis[4-methoxy-

Chemical Property:

• Boiling Point: 368.6°Cat760mmHg
• Flash Point: 124.5°C
• Density: 1.088g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Benzene,1,1'-[oxybis(methylene)]bis[4-methoxy-, also known as bis(4-methoxybenzyl)ether, is a para-methoxybenzyl (PMB) ether derivative widely used as a protecting group for alcohols in organic synthesis. The compound's utility stems from its stability under diverse chemical conditions, making it suitable for protecting sensitive substrates, including α-hydroxy ketones and acid-sensitive epoxy alcohols. Its formation can be efficiently catalyzed by lanthanum triflate, which offers high yields, mild reaction conditions, and compatibility with temperature-sensitive reactions. This highlights its importance in synthetic chemistry for robust and selective alcohol protection.

Technology Process of Benzene,1,1'-[oxybis(methylene)]bis[4-methoxy-

There total 52 articles about Benzene,1,1'-[oxybis(methylene)]bis[4-methoxy- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

trimethyl(4-methoxybenzyloxy)silane (14629-56-2) → 4,4'-dimethoxydibenzyl ether (5405-95-8)

Guidance literature:

With sulfuric acid; silica gel; In hexane; at 20 ℃; for 0.25h;

DOI:10.1055/s-2003-41469

Reference yield: 91.9%

Octanethiol (111-88-6) + 4-Methoxybenzyl alcohol (105-13-5) → 4,4'-dimethoxydibenzyl ether (5405-95-8) + (4-methoxybenzyl)(octyl)sulfane

Guidance literature:

In neat (no solvent); at 110 ℃; for 1h; Temperature; Catalytic behavior; Green chemistry;

DOI:10.3762/bjoc.12.259

Reference yield: 89.0%

4-methoxy-benzaldehyde (123-11-5) → 4,4'-dimethoxydibenzyl ether (5405-95-8)

Guidance literature:

With iodine; In dichloromethane; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.10.063

upstream raw materials:

4-methoxy-benzaldehyde

4-Methoxybenzyl alcohol

4-phenyl-butan-1-ol

diethyl ether

Downstream raw materials:

p-methylanizole

4-methoxy-benzaldehyde

butyl (4-methoxyphenyl)methyl ether

4-Methoxybenzyl alcohol

Refernces

An efficient method for para-methoxybenzyl ether formation with lanthanum triflate

10.1016/S0040-4039(03)00282-X

The study presents an efficient method for the formation of para-methoxybenzyl (PMB) ethers using trichloroacetimidate of PMB alcohol and lanthanum triflate. The PMB group is widely used as a protecting group for alcohols due to its robustness under various chemical conditions. The authors explored different catalysts and solvents to find milder conditions for the protection of alcohols, especially those sensitive to basic conditions. They discovered that lanthanum triflate, among other metal triflates, is highly effective in catalyzing the formation of PMB ethers, allowing for high yields and short reaction times. The study tested various alcohols, including α-hydroxy ketones, glucose derivatives, and acid-sensitive epoxy alcohols, demonstrating the versatility and mildness of the method. The use of lanthanum triflate enabled the protection of even sensitive substrates under low-temperature conditions, highlighting its potential for practical applications in organic synthesis.