Oxalyl chloride → Acetic acid 4-chlorocarbonyl-2,6-dimethyl-phenyl ester

HRID 1846270Notes

Reaction equation

HRID 1846270 reaction equation
[C:1]([O:4][C:5]1[C:13]([CH3:14])=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[CH3:15])(=[O:3])[CH3:2].C(Cl)(=O)C([Cl:19])=O>ClCCl.CN(C=O)C>[Cl:19][C:9]([C:8]1[CH:12]=[C:13]([CH3:14])[C:5]([O:4][C:1](=[O:3])[CH3:2])=[C:6]([CH3:15])[CH:7]=1)=[O:10]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 187041893,5-Dimethyl-4-acetoxybenzoic acid

Product 1

HCID 18704177Acetic acid 4-chlorocarbonyl-2,6-dimethyl-phenyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-acetoxy-3,5-dimethylbenzoic acid (2.08 g, 10.0 mmol) in anhydrous dichloromethane (40 mL) were sequentially added oxalyl chloride (3.81 g, 30.0 mmol) and anhydrous DMF (5 drops). The reaction mixture was stirred at room temperature for 6 hours. Solvent and excess oxalyl chloride were evaporated under reduced pressure and the residue was dried under vacuum to give acetic acid 4-chlorocarbonyl-2,6-dimethylphenyl ester (3) as an orange solid. Yield: 2.32 g (100%).

Workup

  1. customSolvent and excess oxalyl chloride were evaporated under reduced pressure
  2. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-e5691963917d42f188b6de7a88cd610f
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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