Dimethylformamide → 2-(2-Naphthyl)acetyl chloride

HRID 2355134Notes

Reaction equation

HRID 2355134 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1CC(O)=O.CN(C=O)C>C(Cl)Cl>[CH:15]1[C:16]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:14]=1[CH2:1][C:2]([Cl:4])=[O:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 113932-Naphthaleneacetic acidHCID 65578Oxalyl chloride

Product 1

HCID 5881152-(2-Naphthyl)acetyl chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (7.0 mL, 80.2 mmol) was added under nitrogen to a solution of 2-naphthylacetic acid (3.00 g, 16.1 mmol) in 150 mL of methylene chloride at room temperature. A catalytic amount of DMF (10 μL) was added and the reaction stirred at room temperature for 3 h. The solvent and excess oxalyl chloride were removed under reduced pressure. To remove any residual oxalyl chloride the residue was taken up in benzene and then concentrated under reduced pressure to give naphthalen-2-yl-acetyl chloride (3.20 g, 99%) as a yellow solid that was used in the next step without additional purification

Workup

  1. customThe solvent and excess oxalyl chloride were removed under reduced pressure
  2. customTo remove any residual oxalyl chloride the residue
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c9dff9cad6884695b721a7ea1abcbc97
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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