3-Ethylphenol → 4-Ethyl-2-hydroxybenzaldehyde

HRID 859630

Reaktionsgleichung

Reaktionsgleichung von HRID 859630
C[O:2][CH:3](Cl)Cl.[CH2:6]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[CH3:7]>[Ti](Cl)(Cl)(Cl)Cl>[CH2:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:10]=[O:14])=[C:3]([OH:2])[CH:9]=1)[CH3:7]

Komponenten

4

Edukt 2

HCID 121013-EthylphenolHCID 21004Methane, dichloromethoxy-

Produkt 1

HCID 102360174-Ethyl-2-hydroxybenzaldehydeAusbeute 65,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24193Titanium TetrachlorideKatalysator

Versuchsvorschrift

Titanium(IV) chloride (100 mL, 100 mmol, 1M in CH2Cl2) followed by dichloromethyl methyl ether (7.47 mL, 82.5 mmol) was added to a cooled 0° C. solution of 3-ethylphenol (6.11 g, 50 mmol). The reaction mixture was stirred for 45 mins. The mixture was poured into ice and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a bright pink oil. Purification by flash column chromatography (0% to 10% EtOAc in hexanes) gave 4-ethyl-2-hydroxy-benzaldehyde (4.9 g, 65%) followed by 2-ethyl-4-hydroxy-benzaldehyde (1.32 g, 18%). A:

Aufarbeitung

  1. additionThe mixture was poured into ice
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a bright pink oil
  6. customPurification by flash column chromatography (0% to 10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ca05cc5dc4a9443b8cc8728d67940992
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07151105B2

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