Oxalyl chloride → 3,4,5-Trimethoxyphenyl-2-oxoacetyl chloride

HRID 2415045Notes

Reaction equation

HRID 2415045 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:17])[C:14](O)=[O:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(Cl)(=O)C([Cl:21])=O>C(Cl)Cl.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:17])[C:14]([Cl:21])=[O:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 111283972-oxo-2-(3,4,5-trimethoxyphenyl)acetic Acid

Product 1

HCID 226400793,4,5-Trimethoxyphenyl-2-oxoacetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A stirred suspension of 3,4,5-trimethoxyphenyl-2-oxoacetic acid (1.60 g, 6.66 mmoles) in dry methylene chloride (26 mL) at room temperature was treated with 2M oxalyl chloride in methylene chloride (14 mL, 4 equiv.) and dry dimethylformamide (1 drop). After 3 h the solvents were evaporated. The residue was flushed with dry methylene chloride (3×50 mL) and dried in vacuo for 2 h during which time a solid formed. The crude acid chloride was carried on without further purification.

Workup

  1. customAfter 3 h the solvents were evaporated
  2. customThe residue was flushed with dry methylene chloride (3×50 mL)
  3. customdried in vacuo for 2 h during which time a solid
  4. customformed
  5. customThe crude acid chloride was carried on without further purification

Sources & evidence

ORD record
ord-30d3d369eb614c6bb7827fe36fdc3b8d
Source dataset
uspto-grants-2004_11
Patent number
US06818643B1

Reaction notes

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