ChemicalBook CAS DataBase List 3,5-Dimethoxybenzyl chloride

3,5-Dimethoxybenzyl chloride synthesis

6synthesis methods

Product Name:3,5-Dimethoxybenzyl chloride
CAS Number:6652-32-0
Molecular formula:C9H11ClO2
Molecular Weight:186.64

705-76-0
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$10.00/1g

6652-32-0
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$25.00/250mg

Yield: 97%

Reaction Conditions:

with pyridine;thionyl chloride in diethyl ether at 20;Cooling with ice;

Steps:

3,5-Dimethoxybenzyl chloride (5)
A round-bottomed flask (500 mL) equipped with magnetic stirring bar and addition funnel was charged with 4 (16.8 g, 100 mmol), pyridine (0.5 mL) and Et₂O (250 mL). The mixture was cooled in an ice bath while the funnel was charged with SOCl₂ (14.75 g, 1.25 equiv). The addition was made dropwise over 30 min. The ice bath was removed and the mixture was allowed to stir at rt for 12 h. The mixture was poured into H₂O (500 mL) and extracted with Et₂O (3 X 100 mL). The extracts were combined and washed H₂O (2 X 200 mL) followed by brine (200 mL). After drying over anhydrous MgSO₄ the solution was rotary evaporated leaving compound 5 an off-white solid that required no further purification (18.1 g, 97%). Mp 40-42 °C [lit.^Adams 46 °C]. ¹H NMR (CDCl₃): δ 6.53 (d, J = 2.2 Hz, 2H), 6.40 (t, J = 2.2 Hz, 1H), 4.49 (s, 2H), 3.78 (s, 6H); ¹³C NMR (CDCl₃): δ 161.14, 139.70, 106.65, 100.63, 55.53, 46.49.

References:

Davis, Matthew C.;Groshens, Thomas J. [Tetrahedron Letters,2012,vol. 53,# 27,p. 3521 - 3523] Location in patent:supporting information; experimental part

2150-37-0 Synthesis