Sulfuric Acid → Methyl 3-(2-nitrophenyl)prop-2-enoate

HRID 1919552

반응식

HRID 1919552 반응식
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH:6]=[CH:7][C:8]([OH:10])=[O:9])([O-:3])=[O:2].S(=O)(=O)(O)O.[C:20](=O)(O)[O-].[Na+]>CO>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH:6]=[CH:7][C:8]([O:10][CH3:20])=[O:9])([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 928203-(2-Nitrophenyl)acrylic acidHCID 516892Sodium Bicarbonate

생성물 1

HCID 220809Methyl 3-(2-nitrophenyl)prop-2-enoate수율 99%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
70 °C

실험 절차

To a solution of 2-nitrocinnamic acid (7) (10.38 g, 53.76 mmol) dissolved in methanol (200 ml) was dropped a small amount of concentrated sulfuric acid at room temperature, and the reaction mixture was stirred at 70° C. for 12 hours. After the reaction was completed, the resulting solution was basified with a saturated aqueous solution of sodium bicarbonate to weak basicity and extracted with dichloromethane three times. Then, the organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate:hexane=1:5) to give the target compound (11.03 g, 99%).

후처리

  1. extractionextracted with dichloromethane three times
  2. dry with materialThen, the organic phase was dried with anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure

출처 및 근거

ORD 기록
ord-c1436bb127a94893a4c68dc8296ea40f
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168646B2

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