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

HRID 1919552

反応式

HRID 1919552 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-c1436bb127a94893a4c68dc8296ea40f
出典データセット
uspto-grants-2012_05
特許番号
US08168646B2

関連ノート

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