3-Hydroxybenzaldehyde → 3-Isopropoxybenzaldehyde

HRID 48070

Reaktionsgleichung

Reaktionsgleichung von HRID 48070
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].I[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].O>C(O)(C)C>[CH:11]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])([CH3:13])[CH3:12]

Komponenten

6

Edukt 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium Carbonate

Produkt 1

HCID 7129143-IsopropoxybenzaldehydeAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Ex-645A) 3-Hydroxybenzaldehyde (5.60 g, 45.9 mmol) and 2-iodopropane (7.86 g, 46.2 mmol) were dissolved in 50 mL of isopropanol. Potassium carbonate (20 g, 145 mmol) was added, and the mixture was heated to reflux for 8 h, at which time TLC analysis indicated that the reaction had gone to completion. Water was added to dissolve all solids, and the mixture was extracted with ether (3×). The combined ether layer was washed with water, 2 M NaOH, again with water until clear (4×), and finally with brine. The solution was dried over MgSO4, filtered, and evaporated to give 5.03 g (67%) of the desired 3-isopropoxybenzaldehyde product as a pale oil. 1H NMR (C6D6) δ9.62 (s, 1H), 7.29 (s, 1H), 7.03 (m, 1H), 6.91 (t, 1H), 6.84 (m, 1H), 4.03 (septet, 1H), 0.96 (d, 6H).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 8 h, at which time TLC analysis
  3. dissolutionto dissolve all solids
  4. extractionthe mixture was extracted with ether (3×)
  5. washThe combined ether layer was washed with water, 2 M NaOH, again with water until clear (4×)
  6. dry with materialThe solution was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9875bb0e6b004f91984fa7af87dd41f1
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699898B2

Verknüpfte Notizen

Wird geladen…