Toluene → Diethyl 2-[[4-(methylthio)phenyl]methylene]propanedioate

HRID 231202

반응식

HRID 231202 반응식
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:11]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C1(C)C=CC=CC=1>N1CCCCC1.C(O)(=O)C.O>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5][CH:4]=1

참가 물질

7

반응물 3

HCID 1140TolueneHCID 7761Diethyl MalonateHCID 769854-(Methylthio)benzaldehyde

생성물 1

HCID 13221107Diethyl 2-[[4-(methylthio)phenyl]methylene]propanedioate

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 8082Piperidine촉매HCID 962Water용매

실험 절차

4-(Methylthio)Benzaldehyde (3.04 g, .02 mol), diethyl malonate (3.20 g. .02 mol), toluene (25 mL), piperidine (4 drops) and acetic acid (2 drops) are mixed and heated at reflux for 2 hours with the water formed being removed azeotropically. The solution is cooled and 25 mL of water added stirring. After separation of the layers, the toluene is evaporated from the organic layer to yield the product, diethyl 2-[[4-(methylthio)phenyl]methylene]propanedioate, in essentially quantitative yield. When dissolved in methylene chloride, the product has an absorption maximum (λmax) at 330 nm in the ultraviolet absorption spectrum. The identity of the product is confirmed by mass spectroscopy analysis.

후처리

  1. temperatureheated
  2. customformed
  3. custombeing removed azeotropically
  4. temperatureThe solution is cooled
  5. addition25 mL of water added
  6. customAfter separation of the layers
  7. customthe toluene is evaporated from the organic layer

출처 및 근거

ORD 기록
ord-77b5d0c0f78b4a40a24f9e1c86dcdda1
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845188

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