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

HRID 555529Notes

Reaction equation

HRID 555529 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

The compound 3,5-dimethyl-4-hydroxybenzoic acid (5.04 g, 30.33 mmol) was mixed with pyridine (20 mL). Acetic anhydride (3.72 g, 36.4 mmol) was added and the mixture was stirred at room temperature for 4 h. The solvent was evaporated in vacuo to obtain 4-acetoxy-3,5-dimethyl-benzoic acid in quantitative yield (6.33 g). The compound 4-acetoxy-3,5-dimethyl-benzoic acid (0.36 g, 1.73 mmol)) was dissolved in dichloromethane (5 mL) and oxalyl chloride (0.3 mL, 3.46 mmol) was added dropwise, followed by 1 drop of DMF. The reaction mixture was stirred at room temperature under nitrogen for 2 h. The solvent was evaporated in vacuo to obtain acetic acid 4-chlorocarbonyl-2,6-dimethyl-phenyl ester in quantitative yield (0.392 g).

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-44d778b1377c4cc7b02c97dc4128993f
Source dataset
uspto-grants-2011_11
Patent number
US08053440B2

Reaction notes

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