ChemicalBook CAS DataBase List 4-Chlorobenzaldehyde

4-Chlorobenzaldehyde synthesis

14synthesis methods

Product Name:4-Chlorobenzaldehyde
CAS Number:104-88-1
Molecular formula:C7H5ClO
Molecular Weight:140.57

4-Chlorobenzaldehyde can be obtained by chlorinated hydrolysis of p-chlorotoluene: add p-chlorotoluene and phosphorus trichloride to the reaction pot, raise the temperature to 155°C under light and pass chlorine. Control the temperature at 160-170℃ and pass chlorine to the calculated amount to obtain the chlorination solution. Add it to concentrated sulfuric acid with stirring, and stir for 5h at room temperature. let it stand and stratify, take the lower layer into ice water to crystallize, and filter it when it is cold to below 5℃. The filter cake was washed with ice water to obtain the crude product, distilled under reduced pressure and collected 108-111℃ (3.33kPa) fraction to obtain p-chlorobenzaldehyde.

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Yield:104-88-1 100%

Reaction Conditions:

with trichloroisocyanuric acid in acetonitrile; for 0.166667 h;Reflux;

Steps:

Experimental

General procedure: Typical procedure for the one-pot synthesis of 1-chloro-4-dichloromethylbenzene from 4-chlorobenzyl trimethylsilyl ether using TCCA and PPh3: 4-Chlorobenzyl trimethylsilyl ether (0.22 g, 1 mmol) was added to a flask containing TCCA (0.3 g, 1.3 mmol) in acetonitrile (5 mL) as solvent. The reaction mixture was stirred under reflux conditions until TLC showed the completion of the aldehyde formation (10 min). Then, PPh3(0.65 g, 2.5 mmol) was added to the reaction mixture andstirring was continued under reflux until TLC showed the completion of the reaction (80 min). The solvent was evaporatedby rotary evaporator. The crude mixture was subjectedto short column chromatography on silica gel 60(0.063-0.200mm) using n-hexane as eluent affording 1-chloro-4-dichloromethylbenzene as product in 95% yield,0.19 g.

References:

Khadem Moghaddam, Roqayeh;Aghapour, Ghasem [Phosphorus, Sulfur and Silicon and the Related Elements,2020,vol. 196,# 4,p. 398 - 406]