1-chloro-4-(ethoxymethyl)benzene synthesis

11synthesis methods

Product Name:1-chloro-4-(ethoxymethyl)benzene
CAS Number:33598-76-4
Molecular formula:C9H11ClO
Molecular Weight:0

2031-62-1
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104-88-1 Synthesis

104-88-1
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33598-76-4
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Yield:33598-76-4 91%

Reaction Conditions:

Stage #1: diethoxymethylane;4-chlorobenzaldehydewith dicarbonyl(pentamethylcyclopentadienyl)(4-methoxyphenyl)iron in dichloromethane; for 4 h;Inert atmosphere;Irradiation;Schlenk technique;
Stage #2: with sodium hydroxide in methanol;water;Inert atmosphere;Schlenk technique;

Steps:

General procedure for the reaction of aromatic aldehydes and analytical data

General procedure: In a Schlenk tube under 1 atm of argon, a solution of the substrate (2 mmol, 1 equiv), the precatalyst (0.04 mmol, 0.02 equiv), and the silane (3 mmol, 1.5 equiv) in methylene chloride (15 mL) was irradiated for 4h. After removal of the solvent, methanol (5 mL) and aqueous NaOH solution (2.5 M, 5 mL) were added and the resulting suspension was stirred overnight. Neutralization with aqueous HCl solution (2 M, 30 mL) and brine (20 mL) followed by standard workup gave the desired products as pure yellow oils.

References:

Argouarch, Gilles;Grelaud, Guillaume;Roisnel, Thierry;Humphrey, Mark G.;Paul, Frédéric [Tetrahedron Letters,2012,vol. 53,# 37,p. 5015 - 5018] Location in patent:supporting information

78-39-7 Synthesis