Malonic Acid → 3-(4-Methoxy-2-nitrophenyl)prop-2-enoic acid

HRID 1914694

反応式

HRID 1914694 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17].N1CCCCC1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:15]/[C:16]([OH:18])=[O:17])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1

参加物

5

反応物 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 3576914-Methoxy-2-nitrobenzaldehyde

生成物 1

HCID 241789753-(4-Methoxy-2-nitrophenyl)prop-2-enoic acid収率 65.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
125 °C

実験手順

To a mixture of 4-methoxy-2-nitrobenzaldehyde (20 g, 0.11 mol) and malonic acid (28.8 g, 0.28 mol) in pyridine (200 mL) is added piperidine (1 mL, catalytic amount) and the mixture is refluxed at 125° C. under nitrogen for 12 h. After cooling to room temperature, the solvent is removed under reduced pressure and the residue is acidified with 1.5 N HCl. The product is extracted with EtOAc and the organic layer is washed with water and brine then dried over Na2SO4. The solvent is removed under reduced pressure to afford 16 g (65%) of the title compound as a pale brown solid. 1H NMR (DMSO-d6, 400 MHz) δ 12.59 (bs, 1H), 7.91-7.93 (m, 1H), 7.68-7.72 (m, 1H), 7.56 (s, 1H), 7.31-7.33 (m, 1H), 7.46-7.50 (m, 1H), 3.87 (s, 3H).

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe solvent is removed under reduced pressure
  3. extractionThe product is extracted with EtOAc
  4. washthe organic layer is washed with water and brine
  5. dry with materialthen dried over Na2SO4
  6. customThe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-315012fc6e5c405ab69ae3c513dfde0a
出典データセット
uspto-grants-2013_12
特許番号
US08614215B2

関連ノート

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