Dichloromethane → 3-Ethoxy-4-methoxybenzoyl chloride

HRID 238060Notes

Reaction equation

HRID 238060 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7](O)=[O:8])[CH3:2].C(Cl)[Cl:16].C(Cl)(=O)C(Cl)=O>CN(C=O)C.C1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7]([Cl:16])=[O:8])[CH3:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 28229573-Ethoxy-4-methoxybenzoic acid

Product 1

HCID 450812503-Ethoxy-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

3-ethoxy-4-methoxybenzoic acid (5 g, 25.5 mmol) was added to a solution of CH2Cl2 (40 mL) and benzene (20 mL) in a flame-dried 150 mL round bottom flask. Anhydrous DMF (9 drops) was added and the solution was cooled on ice. Oxalyl chloride (11 mL, 128 mmol) was added dropwise, and the reaction was then allowed to warm to RT. The reaction was stirred at RT for 90 minutes, then concentrated in vacuo yield an off-white solid. The solid was placed on a high-vacuum line for 2 hours, and then taken onto the next step without further characterization.

Workup

  1. temperaturethe solution was cooled on ice
  2. concentrationconcentrated in vacuo
  3. customyield an off-white solid
  4. waitThe solid was placed on a high-vacuum line for 2 hours

Sources & evidence

ORD record
ord-1f03044187f647448e95fefc29def7e7
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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