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