Acetic Acid → 4-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

HRID 482007

Reaktionsgleichung

Reaktionsgleichung von HRID 482007
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:16])[CH2:12]CC#N)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:17]([OH:20])(=[O:19])[CH3:18]>Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:16])[CH2:12][CH2:18][C:17]([OH:20])=[O:19])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

4

Edukt 2

HCID 176Acetic AcidHCID 124916314-(3,4-Dimethoxyphenyl)-4-oxobutanenitrile

Produkt 1

HCID 2193904-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A stirred solution of 4-(3',4'-dimethoxyphenyl)-4-oxobutyronitrile (111) (2.26 g, 0.01 mol) in acetic acid (15 ml) and hydrochloric acid (12N, 40 ml) was heated at reflux for 1.5 hours and cooled to room temperature. The solvent was removed under reduced pressure to give a brown solid. Recrystallization from water gave 112 as light tan crystals (1.57 g, 66%). 1H NMR (CDCl3) 2.80 (t, J=7.5 Hz, 2H), 3.30 (t, J=7.5 Hz, 2H), 3.94 (s, 3H), 3.96 (s, 3H), 6.89 (d, 1H, J=9 Hz), 7.55 (d, 1H, J=1 Hz) and 7.64 (dd, 1H, 1 and 9 Hz).

Aufarbeitung

  1. temperatureat reflux for 1.5 hours
  2. customThe solvent was removed under reduced pressure
  3. customto give a brown solid
  4. customRecrystallization from water

Quellen und Nachweise

ORD-Eintrag
ord-a3430dbd91cd4846a6af4030c3ab5be6
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792776

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