Reaction #2329039

Reaction equation

Thionyl chloride

4-Dodecyloxybenzyl alcohol

DMF

→

benzyl chloride

4-Dodecyloxybenzyl Chloride

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONUpon addition, reaction
2. 2
   OtherReaction mixture
3. 3
   Concentrationwas concentrated under reduced pressure
4. 4
   Otherthe resulting residue re-crystallized from acetone

Procedure

Thionyl chloride (38.8 g, 328 mmol) was added dropwise to a 0° C. solution of 4-Dodecyloxybenzyl alcohol (80.0 g, 274 mmol) in dry CH2Cl2 (900 mL) with a catalytic amount of DMF. Upon addition, reaction was allowed to stir for 5-10 minutes, while monitoring through TLC (CH2Cl2) for completion. Reaction mixture was concentrated under reduced pressure and the resulting residue re-crystallized from acetone to give the title benzyl chloride, decomposes upon melting. 77g (92%).

Source