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ChemicalBook CAS DataBase List Benzyl chloride
100-44-7

Benzyl chloride synthesis

13synthesis methods
2g benzyl alcohol and 6g concentrated hydrochloric acid were mixed and slowly heated. at 60°C the mixture separated into two layers. the yield of benzyl chloride was 70% of the theoretical. When the alcohol and a large excess of the acid were mixed, the reaction took place at the room temperature after a few minutes, and a theoretical yield of the chloride separated. Benzyl alcohol dissolves sparingly in hydrochloric acid of the specific gravity 1.12. when the solution is warmed, benzyl chloride is formed. Benzyl bromide and benzyl iodide were prepared in the same way from the corresponding acids.
benzyl chloride is a lachrymator, and a powerful one at that. In the presence of water, it hydrolyzes to benzyl alcohol and hydrochloric acid, so it's clear why it burns your water saturated eye so bad.
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Yield:100-52-7 84.7% ,100-44-7 6.3%

Reaction Conditions:

Stage #1: benzyl alcoholwith oxalyl dichloride;dimethyl sulfoxide at 15;Flow reactor;Swern Oxidation;
Stage #2: with triethylamine at 15;Flow reactor;Swern Oxidation;Temperature;

Steps:

3.2. Experimental procedure

General procedure: The continuous ow microreactor system was assembled as shown in Figure 1. The Me2SO, activator, and benzyl alcohol were loaded into HPLC pumps with appropriate ow rates. After a stable period of 10 min, the effluent was collected in a separation funnel through which we could observe the color and layering by controlling the valve. Then effluent was finally collected into a continuously stirred ask containing an excess amount of triethylamine. The temperatures were kept constant by a water bath with constant circulation temperatures and a thermostat magnetism agitator. All of the reactions were monitored offline by GC-MS; the yields and selectivities were calculated by the method of area normalization. Upon completion of the reaction, the mixture of triethylamine and effluent was washed with 5% HCl and the organic layer was separated. Then the organic layer was washed 2 or 3 times until the mixture in the separation funnel reached neutral. In the process, the aqueous layers were always extracted twice with dichloromethane. At last, the organic layers were collected together and dried by anhydrous MgSO4 for 4 h. The final product, benzaldehyde, was obtained after filtration and reduced pressure distillation.

References:

Zhu, Lin;Xu, Xiaohui;Zheng, Fuping [Turkish Journal of Chemistry,2018,vol. 42,# 1,p. 75 - 85]

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