Reaction #2329035

Reaction equation

Thionyl chloride

4-ethoxybenzyl alcohol

DMF

→

4-Ethoxybenzyl 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
   workup.DISSOLUTIONthe residue dissolved in minimal THF
5. 5
   Otherprecipitated in cold H2O
6. 6
   Otherto yield a white precipitate
7. 7
   OtherThe solid was collected
8. 8
   Otherdried
9. 9
   Concentrationconcentrated
10. 10
    Temperatureby cooling with CO2/acetone

Procedure

Thionyl chloride (10.4 g, 87.7 mmol) was added dropwise to a 0° C. solution of 4-ethoxybenzyl alcohol (11.0 g, 72.4 mmol) in dry CH2Cl2 (150 mL) with a catalytic amount of DMF (1 mL). 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 residue dissolved in minimal THF and then precipitated in cold H2O to yield a white precipitate. The solid was collected, taken up in CH2Cl2, dried and concentrated. The resulting oil was solidified by cooling with CO2/acetone. The compound as a white solid, which decomposes upon melting 11.3 g(92%).

Source