Thionyl Chloride → 1-(Chloromethyl)-4-(dodecyloxy)benzene

Participants

Reaction Steps

A solution of 4-dodecyloxybenzyl alcohol (Preparation 1, 2.92 g, 0.0010 M) in benzene (40 mL) is added dropwise to a stirred solution of thionyl chloride (3.0 mL, 4.97 g, 0.04 M) over a period of 20 minutes. The solution is stirred at room temperature for 0.5 hr and then is heated at reflux temperature for 3 hours (monitoring of the reaction by TLC may be deceptive since the product is hydrolyzed to starting alcohol when placed on a silica gel plate; the plate must be developed immediately after the sample is applied). Benzene and excess thionyl chloride are removed under reduced pressure. The crude product is used in Example 1 without further purification.

Provenance & Evidence