Benzoic Acid → 4-(Chloromethyl)benzoyl chloride

HRID 847646Notes

Reaction equation

HRID 847646 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)[C:11]([Cl:13])=O.C(Cl)[Cl:17]>CN(C=O)C>[Cl:13][CH2:11][C:5]1[CH:4]=[CH:3][C:2]([C:1]([Cl:17])=[O:9])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 6344DichloromethaneHCID 65578Oxalyl chloride

Product 1

HCID 701364-(Chloromethyl)benzoyl chlorideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

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).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 17 h
  2. concentrationThe reaction mixture was then concentrated in vacuo @45°-50° C
  3. additionadded to the residual oil
  4. customremoved by azeotropic distillation
  5. distillationThe oil was then distilled under reduced pressure

Sources & evidence

ORD record
ord-f00670be3d9d4863b77ee7cfcee6931f
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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