Dimethylformamide → 4-(2-chloroethoxy)benzoyl Chloride

HRID 2289157Notes

Reaction equation

HRID 2289157 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1.CN(C)C=O.C(Cl)(=O)C([Cl:22])=O>ClCCCl>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:22])=[O:10])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 123892684-(2-Chloroethoxy)benzoic acid

Product 1

HCID 110748714-(2-chloroethoxy)benzoyl Chloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a 250-ml flask are combined 4-(2-chloroethoxy)benzoic acid (2.58 g, 12.9 mmol), dimethylformamide (0.2 ml) and 1,2-dichloroethane (50 ml). Oxalyl chloride (1.35 ml) is added dropwise and the reaction mixture stirred overnight at room temperature. The reaction becomes homogeneous after stirring several hours. After an overnight stir, the solvent is evaporated to dryness, and the solid product is redissolved in 1,2-dichloroethane (2×50 mL) and evaporated. The product is used as is in subsequent reactions.

Workup

  1. customIn a 250-ml flask are combined
  2. stirringafter stirring several hours
  3. stirringAfter an overnight stir
  4. customthe solvent is evaporated to dryness
  5. dissolutionthe solid product is redissolved in 1,2-dichloroethane (2×50 mL)
  6. customevaporated

Sources & evidence

ORD record
ord-865766fccdd6458aa3d514b217c001c8
Source dataset
uspto-grants-2000_07
Patent number
US06090949

Reaction notes

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