Methyl iodide → p-Methoxyphenylpropionic acid

HRID 638107ノート

反応式

HRID 638107 の反応式
[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]

参加物

9

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 4

HCID 23939Platinum触媒HCID 2734932Tetraethylammonium perchlorate触媒2 回HCID 6228Dimethylformamide溶媒HCID 31374Dimethylacetamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d86c8b8b9a5740679816f81873ea522c
出典データセット
uspto-grants-1985_12
特許番号
US04560447

反応ノート

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