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

HRID 488545노트

반응식

HRID 488545 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3f9e75f601d24736b5764f03b2d30c0e
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06972339B2

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