Methyl iodide → p-Methoxyphenylpropionic acid

HRID 638107

반응식

HRID 638107 반응식
[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]

참가 물질

9

반응물 3

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 90266Methyl 4-methoxyphenylacetate2회

생성물 2

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

시약·촉매·용매 4

HCID 23939Platinum촉매HCID 2734932Tetraethylammonium perchlorate촉매2회HCID 6228Dimethylformamide용매HCID 31374Dimethylacetamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d86c8b8b9a5740679816f81873ea522c
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04560447

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