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ChemicalBook CAS DataBase List 5-(Chloromethyl)-1,2,3-trimethoxybenzene

5-(Chloromethyl)-1,2,3-trimethoxybenzene synthesis

7synthesis methods
-

Yield:3840-30-0 87%

Reaction Conditions:

with pyridine;thionyl chloride in dichloromethane at 20; for 1.5 h;

Steps:

1.1.3. Synthesis of 3,4,5-trimethoxybenzyl chloride (Scheme 1)
To the solution of 3,4,5-trimethoxybenzyl alcohol (7.2 g, 36.4 mol) in dry DCM (100 mL), thionyl chloride (3.5 mL, 48.2 mmol) and pyridine (3.4 mL, 42.1 mmol) were added dropwise. The reaction mixture was stirred at RT for 1.5 h and progress was monitored by TLC (AcOEt/Hex 1:1 as mobile phase). The reaction was stopped by the addition of 100 mL H2O and extracted with 2 x 25 mL DCM. The combined organic extracts were dried over MgSO4 and evaporated in vacuo to give 87% yield. Yellow, solid.

References:

Urbaniak, Alicja;Delgado, Magdalena;Kacprzak, Karol;Chambers, Timothy C. [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 12,p. 2766 - 2770] Location in patent:supporting information

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