Oxalyl chloride → 3-Methoxy-4-methoxycarbonylbenzoyl chloride

HRID 442790Notes

Reaction equation

HRID 442790 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]([O:14][CH3:15])=[O:13])[C:6](O)=[O:7].C(Cl)(=O)C([Cl:19])=O>ClCCl.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]([O:14][CH3:15])=[O:13])[C:6]([Cl:19])=[O:7]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 123983053-Methoxy-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 151619683-Methoxy-4-methoxycarbonylbenzoyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 3-methoxy-4-methoxycarbonylbenzoic acid (4.1 g, 19.5 mmol) and oxalyl chloride (2.4 ml, 27.3 mmol) in dry dichloromethane (100 ml) was added 2 drops of dimethylformamide. After 3 h at room temperature the clear solution was evaporated to an oil. The oil was redissolved in dry dichloromethane and evaporated, this procedure was repeated to give 3-methoxy-4-methoxycarbonylbenzoyl chloride as an oil (100%) which was used immediately in the next step.

Workup

  1. customAfter 3 h at room temperature the clear solution was evaporated to an oil
  2. dissolutionThe oil was redissolved in dry dichloromethane
  3. customevaporated

Sources & evidence

ORD record
ord-36a07b2b858d4200ac04132ab2bc1bef
Source dataset
uspto-grants-1999_04
Patent number
US05891899

Reaction notes

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