(2-Ethoxy-3-isopropylphenyl)methanol → 2-Ethoxy-3-isopropylbenzaldehyde

HRID 2097033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2097033
[CH2:1]([O:3][C:4]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13][OH:14])[CH3:2]>C1C=CC=CC=1.O=[Mn]=O>[CH2:1]([O:3][C:4]1[C:9]([CH:10]([CH3:11])[CH3:12])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:13]=[O:14])[CH3:2]

Komponenten

4

Edukt 1

HCID 59277552(2-Ethoxy-3-isopropylphenyl)methanol

Produkt 1

HCID 592775432-Ethoxy-3-isopropylbenzaldehydeAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

MnO2 (9.49 g, 109 mmol) was added to a stirring solution of (2-ethoxy-3-isopropylphenyl)methanol (3.54 g, 18.2 mmol) in benzene (175 mL) under N2. After stirring for 48 h, the solution was filtered over diatomaceous earth and the pad rinsed with CH2Cl2 (200 mL), and the solution was concentrated to a clear oil. Purification by column chromatography (silica gel, hexanes/EtOAc, 100 to 98:2) gave the title compound (1.49 g, 42%) as a light yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 7.67 (dd, J=7.6, 1.7 Hz, 1H), 7.59 (dd, J=7.6, 1.7 Hz, 1H), 7.28 (t, J=7.6 Hz, 1H), 3.97 (q, J=6.9 Hz, 2H), 3.32-3.30 (m, 1H), 1.39 (t, J=6.9 Hz, 3H), 1.21 (d, J=6.9 Hz, 6H).

Aufarbeitung

  1. filtrationthe solution was filtered over diatomaceous earth
  2. washthe pad rinsed with CH2Cl2 (200 mL)
  3. concentrationthe solution was concentrated to a clear oil
  4. customPurification by column chromatography (silica gel, hexanes/EtOAc, 100 to 98:2)

Quellen und Nachweise

ORD-Eintrag
ord-646162bf8f7a402ab09fb3276e8de685
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450307B2

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