Methyl iodide → p-Methoxyphenylpropionic acid

HRID 638107Notes

Reaction equation

HRID 638107 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.[CH3:14]I.[Cl-].[NH4+]>Cl([O-])(=O)(=O)=O.C([N+](CC)(CC)CC)C.CC(N(C)C)=O.CN(C)C=O.[Pt]>[CH3:14][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:10]([O:12][CH3:13])=[O:11].[CH3:14][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:10]([OH:12])=[O:11]

Participants

9

Reactant 3

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 90266Methyl 4-methoxyphenylacetate2×

Product 2

HCID 257576p-Methoxyphenylpropionic acidHCID 12398855Methyl 2-(4-methoxyphenyl)propanoate

Reagents, catalysts & solvents 4

HCID 23939PlatinumCatalystHCID 2734932Tetraethylammonium perchlorateCatalyst2×HCID 6228DimethylformamideSolventHCID 31374DimethylacetamideSolvent

Procedure

Into the cathode chamber of an electrolytic cell divided with a diaphragm (ceramic filter) was placed a solution of 10 mmols of methyl p-methoxyphenylacetate, 12 mmols of methyl iodide and 2.0 g of tetraethylammonium perchlorate in 30 ml of anhydrous dimethylacetamide. And the anode chamber was provided with a solution of 3.0 g of tetraethylammonium perchlorate in 20 ml of anhydrous dimethylformamide. Constant current electrolysis was performed at 0.2 A/cm2 with use of platinum for both the anode electrode and the cathode electrode. After passing 1.5 F of electricity per mol of the methyl p-methoxyphenylacetate through the solution at -5° to 0° C., the cathode solution was added to a saturated aqueous solution of ammonium chloride and the mixture was extracted twice with ether. The ether was distilled off and the residue was purified by silica gel column chromatography using hexane-ethyl acetate (10:1), giving methyl α-methyl-p-methoxyphenylacetate in a yield of 81% and α-methyl-p-methoxyphenylacetic acid in a yield of 10%. The spectral data of the ester were as follows.

Workup

  1. filtrationInto the cathode chamber of an electrolytic cell divided with a diaphragm (ceramic filter)
  2. customat -5° to 0° C.
  3. extractionthe mixture was extracted twice with ether
  4. distillationThe ether was distilled off
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d86c8b8b9a5740679816f81873ea522c
Source dataset
uspto-grants-1985_12
Patent number
US04560447

Reaction notes

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