Dimethylformamide → 3-(Chlorocarbonyl)-6-methoxyphenyl acetate

HRID 1918329Notes

Reaction equation

HRID 1918329 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8](O)=[O:9])(=[O:3])[CH3:2].CN(C=O)C.C(Cl)(=O)C([Cl:24])=O>C(Cl)Cl>[Cl:24][C:8]([C:7]1[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=1)=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 151620Benzoic acid, 3-(acetyloxy)-4-methoxy-

Product 1

HCID 185369263-(Chlorocarbonyl)-6-methoxyphenyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

700 mg of 3-acetoxy-4-methoxy-benzoic acid were suspended in 6 ml of anhydrous DCM and 24 μl of DMF were added. Then 5.0 ml of a 2 M solution of oxalyl chloride in DCM were added dropwise. The mixture was stirred until the evolution of gas had ceased (about 30 min). The volatiles were removed in vacuo, the residue was dissolved in 10 ml of DCM and evaporated to yield 750 mg of the title compound which was used in the subsequent step without further purification.

Workup

  1. custom(about 30 min)
  2. customThe volatiles were removed in vacuo
  3. dissolutionthe residue was dissolved in 10 ml of DCM
  4. customevaporated

Sources & evidence

ORD record
ord-8f7b0d7c73c141f49349f101619b5393
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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