3-Hydroxybenzaldehyde → 3-Isopropoxybenzaldehyde

HRID 501732

Reaktionsgleichung

Reaktionsgleichung von HRID 501732
FC(F)(F)C(N[C@@H:6]1[C:14]2C(=CC=C(OC)C=2)C(=O)[CH2:7]1)=O.[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[O:25].IC(C)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH:6]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[O:25])([CH3:14])[CH3:7]

Komponenten

7

Edukt 4

HCID 1013-HydroxybenzaldehydeHCID 6362Isopropyl iodide2×HCID 11430Potassium Carbonate2×HCID 1472787(S)-2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide

Produkt 1

HCID 7129143-IsopropoxybenzaldehydeAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Step AU (1). A solution of 3-hydroxybenzaldehyde (67 g, 549 mmol), 2-iodopropane (100 g, 588 mmol) and K2CO3 (130 g, 942 mmol) in 400 mL DMF was stirred for 18 h. To the above solution was added 2-iodopropane (20 g, 117 mmol) and K2CO3 (20 g, 145 mmol) and the mixture was stirred for another 24 h. The reaction mixture was poured into 300 mL water which was extracted with EtOAc (200 mL×3). The combined organic layers were washed with water (100 mL×3), dried over Na2SO4, filtered, and concentrated in vacuo to afford 77 g (85% yield) of 3-isopropoxybenzaldehyde as an oil. 1H NMR (300 MHz, CDCl3) δ 1.29-1.31 (d, 6H) 4.5-4.6 (m, 1H) 7.0-7.1 (m, 1H) 7.3-7.4 (m, 3H).

Aufarbeitung

  1. extractionwas extracted with EtOAc (200 mL×3)
  2. washThe combined organic layers were washed with water (100 mL×3)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8571272274344ffcbf958067fbe99d83
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772221B2

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