Ethyl Methanesulfonate → 2-Phenylbutyric Acid

HRID 638105

반응식

HRID 638105 반응식
[C:1]1([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(O[CH2:17][CH3:18])(=O)=O.[Cl-].[NH4+]>S(C1C=CC(C)=CC=1)([O-])(=O)=O.C([N+](CC)(CC)CC)C.CN(C)C=O.[Pt]>[CH2:17]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:18].[CH2:17]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([OH:10])=[O:9])[CH3:18]

참가 물질

8

반응물 3

HCID 6113Ethyl MethanesulfonateHCID 7559Methyl phenylacetate2회HCID 25517Ammonium Chloride

생성물 2

HCID 70122-Phenylbutyric AcidHCID 102780Benzeneacetic acid, alpha-ethyl-, methyl ester

시약·촉매·용매 3

HCID 23939Platinum촉매HCID 101846Tetraethylammonium p-toluenesulphonate촉매2회HCID 6228Dimethylformamide용매2회

실험 절차

Into the cathode chamber of an electrolytic cell divided with an ion-exchange resin diaphragm was placed a solution of 10 mmols of methyl phenylacetate, 12 mmols of ethyl methanesulfonate and 1.0 g of tetraethylammonium tosylate in 30 ml of anhydrous dimethylformamide. And the anode chamber was provided with a solution of 1.0 g of tetraethylammonium tosylate in 10 ml of anhydrous dimethylformamide. Constant current electrolysis was performed at 0.2 A/cm2 with use of platinum for the cathode and carbon for the anode. After passing 1.5 F of electricity per mol of the methyl phenylacetate through the solution at 5 to 10 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-ethylphenylacetate in a yield of 77% and α-ethylphenylacetic acid in a yield of 13%. The spectral data of the ester were as follows.

후처리

  1. extractionthe mixture was extracted twice with ether
  2. distillationThe ether was distilled off
  3. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-3c500045094e49f49dab1007d63f00e8
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04560447

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