2-(4-Methoxyphenyl)butanoic acid → HCID 22918974, compound

HRID 249535Notes

Reaction equation

HRID 249535 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:19][CH3:20])[C:16](O)=[O:17])=[CH:11][CH:10]=1>C(Cl)Cl>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:19][CH3:20])[C:16]([Cl:4])=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 346572-(4-Methoxyphenyl)butanoic acidHCID 65578Oxalyl chloride

Product 1

HCID 22918974HCID 22918974, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (12 mL of a 2.0M solution in CH2Cl2) was added under nitrogen to a solution of 2-(4'-methoxyphenyl)butyric acid (4.66 g, 24 mmol) in 25 mL of CH2Cl2 and stirred at room temperature overnight. The volatiles were removed under vacuum and the residue was distilled to afford 4.46 g (87%) of pure 2-(4'-methoxyphenyl)butyryl chloride. 1H NMR (CDCl3) δ0.919 (t, 3H, J=7.4 Hz), 1.78-1.92 (m, 1H), 2.13-2.27 (m, 1H), 3.81 (s, 3H), 3.83 (t, 1H, J=7.6 Hz), 6.91 (d, 2H, J=8.8 Hz), 7.21 (d, 2H, J=8.7 Hz); 13C NMR (CDCl3) δ11.43, 26.26, 55.14, 64.21, 114.50, 127.86, 129.65, 159.75, 175.48.

Workup

  1. customThe volatiles were removed under vacuum
  2. distillationthe residue was distilled

Sources & evidence

ORD record
ord-ab96c7bd8d5041658a670f9fe26a07a8
Source dataset
uspto-grants-1993_05
Patent number
US05214191

Reaction notes

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