Oxalyl chloride → 3-(4-Nitrophenyl)propionyl chloride

HRID 1003828Notes

Reaction equation

HRID 1003828 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl.CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([Cl:18])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 855263-(4-Nitrophenyl)propanoic acid

Product 1

HCID 147973603-(4-Nitrophenyl)propionyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

3-(4-Nitrophenyl)propanoic acid prepared in Example DD (12.5 g, 64 mmol) was suspended in CH2Cl2 (300 mL) and treated with oxalyl chloride (7.4 mL, 85 mmol) and DMF (5 drops). The solution was stirred overnight at room temperature. The solution was concentrated, and the residue was dissolved in CH2Cl2 and re-concentrated. The crude product was used as is in the next step.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. concentrationre-concentrated

Sources & evidence

ORD record
ord-8ec55a756b9a45e4a6d5632690d81248
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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