2-Methoxy-5-methylphenol → 4-Hydroxy-5-methoxy-2-methylbenzaldehyde

HRID 1187005

Reaktionsgleichung

Reaktionsgleichung von HRID 1187005
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[OH:10].[CH3:11][O:12]C(Cl)Cl>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[OH:10][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([CH:11]=[O:12])=[C:6]([CH3:9])[CH:5]=1

Komponenten

5

Edukt 2

HCID 145192-Methoxy-5-methylphenolHCID 21004Methane, dichloromethoxy-

Produkt 1

HCID 234242834-Hydroxy-5-methoxy-2-methylbenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-methoxy-5-methylphenol (50.0 g, 362 mmol) in CH2Cl2 (1000 mL) at −5° C. were added titanium (IV) chloride (80.0 mL, 724 mmol) slowly via syringe (internal temperature was kept below 0° C. during addition) and dichloromethyl methyl ether (52.9 mL, 593 mmol). After being stirred at room temperature for 3 h, the mixture was poured into ice water. The resulting precipitate was collected by filtration and then washed with EtOAc and Et2O to afford 4-Hydroxy-5-methoxy-2-methylbenzaldehyde. 1H NMR (CDCl3) δ 10.22 (s, 1H), 7.38 (s, 1H), 6.81 (s, 1H), 6.14 (s, 1H), 3.96 (s, 3H), 2.62 (s, 3H); LC/MS: (IE, m/z) (M+1)+=16.0; tR=2.06 min.

Aufarbeitung

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with EtOAc and Et2O

Quellen und Nachweise

ORD-Eintrag
ord-d937d76ecc1a4189875b222024053ee0
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673920B2

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