Sodium Hydroxide → 2-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzaldehyde

HRID 2075056

Reaktionsgleichung

Reaktionsgleichung von HRID 2075056
[CH:1]1([CH:7]([O:20][CH3:21])[C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[CH2:18][OH:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[CH:1]1([CH:7]([O:20][CH3:21])[C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:17])[F:15])=[CH:10][C:9]=2[CH:18]=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 58968734(2-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)phenyl)methanol

Produkt 1

HCID 589686992-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzaldehydeAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)phenyl)methanol (113.1 mg, 0.37 mmol) in methylene chloride (2 mL) at room temperature was added Dess-Martin periodinane reagent (175 mg, 0.41 mmol). The mixture was stirred at room temperature for 1 hour. 1N NaOH was added and the mixture was extracted with ethyl acetate. Combined organic layers were washed with 1N NaOH, brine, dried over sodium sulfate and concentrated in vacuo to yield the title compound (107.2 mg, 95%). 1H NMR (400 MHz, CDCl3) δ ppm 1.07-1.18 (m, 4H) 1.36 (d, J=5.81 Hz, 1H) 1.53-1.69 (m, 4H) 1.71-1.76 (m, J=2.49 Hz, 1H) 1.83-1.90 (m, 1H) 3.22 (s, 3H) 4.73 (d, J=6.22 Hz, 1H) 7.66 (d, J=8.30 Hz, 1H) 7.81 (dd, J=8.30, 1.66 Hz, 1H) 8.14 (s, 1H) 10.41 (s, 1H).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washCombined organic layers were washed with 1N NaOH, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-87eefe1a8ffd4753857f7efe62b895df
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919506B2

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