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

HRID 1047338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047338
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-987c5a5416d446118c3f530f2fea4ebf
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569516B2

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