Benzoic Acid → 4-(Chloromethyl)benzoyl chloride

Participants

Reaction Steps

Benzoic acid (20.0 g, 117 mmol) was suspended in 100 mL of freshly distilled methylene chloride with stirring under a nitrogen atmosphere. Approximately 2 drops of DMF was added to the suspension, followed by the dropwise addition of oxalyl chloride (29.7 g, 234 mmol) over a 0.5 h period. The reaction mixture was stirred at ambient temperature for 17 h. The reaction mixture was then concentrated in vacuo @45°-50° C. Toluene (30 mL) was three times added to the residual oil and removed by azeotropic distillation. The oil was then distilled under reduced pressure to give 20.8 g (94% yield) of the title compound; b.p. 139°-149° C. (12 mm Hg); 1H NMR (CDCl3) d 4.63 (s, 2H), 7.54 (d, 2H), 8.12 (d, 2H).

Provenance & Evidence