2-Ethyl-5-methylphenol → 5-Ethyl-4-hydroxy-2-methyl-benzaldehyde

HRID 1453312

Reaktionsgleichung

Reaktionsgleichung von HRID 1453312
[CH3:1][O:2]C(Cl)Cl.[CH2:6]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[OH:15])[CH3:7]>[Ti](Cl)(Cl)(Cl)Cl>[CH2:6]([C:8]1[C:9]([OH:15])=[CH:10][C:11]([CH3:14])=[C:12]([CH:13]=1)[CH:1]=[O:2])[CH3:7]

Komponenten

4

Edukt 2

HCID 155232-Ethyl-5-methylphenolHCID 21004Methane, dichloromethoxy-

Produkt 1

HCID 587624205-Ethyl-4-hydroxy-2-methyl-benzaldehydeAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24193Titanium TetrachlorideKatalysator

Versuchsvorschrift

Titanium(IV) chloride (11 mL, 11 mmol, 1M in CH2Cl2) followed by dichloromethyl methyl ether (1.04 g, 9.1 mmol) was added to a cooled 0° C. solution of 2-ethyl-5-methyl-phenol (0.75 g, 5.5 mmol) The reaction mixture was stirred for 30 mins and then warmed up to rt and stirred for another 30 mins. The mixture was poured into ice and extracted with EtOAc. The organic layers were washed with satd NaHCO3, brine, dried over Na2SO4 and concentrated to a purple oil. Purification by flash column chromatography (0% to 10% EtOAc in hexanes) gave the title compound as an oil (0.45 g, 50%). 1H NMR (400 MHz, CDCl3): δ 1.26 (t, J=7.6 Hz, 3H), 2.60 (s, 3H), 2.65 (q, J=7.6 Hz, 2H), 5.37 (s, 1H), 6.62 (s, 1H), 7.62 (s, 1H), 10.11 (s, 1H).

Aufarbeitung

  1. stirringstirred for another 30 mins
  2. additionThe mixture was poured into ice
  3. extractionextracted with EtOAc
  4. washThe organic layers were washed with satd NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a purple oil
  7. customPurification by flash column chromatography (0% to 10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-84ffe877848c401fa0f5e22caca0b03b
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473790B2

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