Hydrochloric Acid → 5-Iodo-2,4-dimethoxybenzaldehyde

HRID 10753

Reaktionsgleichung

Reaktionsgleichung von HRID 10753
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[I:13]Cl.Cl>CO>[I:13][C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:3]([O:2][CH3:1])=[C:4]([CH:7]=1)[CH:5]=[O:6]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24640Iodine chlorideHCID 691752,4-Dimethoxybenzaldehyde

Produkt 1

HCID 142459555-Iodo-2,4-dimethoxybenzaldehydeAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 2,4-dimethoxy-benzaldehyde (20.0 g, 120.4 mmol) in methanol (550 mL) was added a solution of iodine monochloride (23.25 g, 144.9 mmol) in methanol (60 mL) dropwise over 20 min. The solution was allowed to stir at ambient temperature for 3 hours and then poured into a solution of hydrochloric acid (0.5 M, 600 mL). The resulting precipitate was collected by filtration, washed with water, and dried in vacuo. The crude product was further recrystallized from a mixture of tetrahydrofuran and heptane (1:1, v/v) to give the title compound as a white solid (30.62 g, 87.5%), m.p. 170–172° C. 1H NMR (CDCl3) δ 10.19 (s, 1H), 8.22 (s, 1H), 6.39 (s, 1H), 3.97 (s, 3H), 3.95 (s, 3H).

Aufarbeitung

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried in vacuo
  4. customThe crude product was further recrystallized from a mixture of tetrahydrofuran and heptane (1:1

Quellen und Nachweise

ORD-Eintrag
ord-e6aaf19072de4abd8400219da961b065
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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