Malonic Acid → 3-(3-Chloro-2,4-dimethoxyphenyl)prop-2-enoic acid

HRID 488545ノート

反応式

HRID 488545 の反応式
[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17].N1CCCCC1>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:5]=[CH:15][C:16]([OH:18])=[O:17])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

参加物

5

反応物 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 133437053-Chloro-2,4-dimethoxybenzaldehyde

生成物 1

HCID 688767863-(3-Chloro-2,4-dimethoxyphenyl)prop-2-enoic acid収率 95%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of compound (2a) (11.07 g, 55.2 mmol), malonic acid (8.639 g, 83 mmol) and piperidine (2 ml, 1.722 g, 20.2 mmol) in 80 ml of anhydrous pyridine was refluxed (bath temperature 110° C.) for 2 h. Reaction mixture was cooled, concentrated under vacuum and acidified 250 ml of 5% aqueous citric acid to a pH of 3. Resulted heterogeneous mixture was sonicated for a few minutes. The precipitated material was filtered off, washed with water (2×20 ml) and dried in vacuum over KOH to give 12.7 g (52.3 mmol, 95% yield) of pure (HPLC, 1H NMR) desired acid 3a as a white solid. 1H NMR (DMSO-d6): δ 7.77 (d, J=9.0 Hz, 1H), 7.67 (d, J=16.0 Hz, 1H), 7.01 (d, J=9.0 Hz, 1H), 6.51 (d, J=16.0 Hz, 1H), 3.90 (s, 3H), 3.77 (s, 3H).

後処理

  1. customReaction mixture
  2. temperaturewas cooled
  3. concentrationconcentrated under vacuum
  4. customResulted heterogeneous mixture
  5. customwas sonicated for a few minutes
  6. filtrationThe precipitated material was filtered off
  7. washwashed with water (2×20 ml)
  8. dry with materialdried in vacuum over KOH

出典と根拠

ORDレコード
ord-3f9e75f601d24736b5764f03b2d30c0e
出典データセット
uspto-grants-2005_12
特許番号
US06972339B2

反応ノート

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