Diethyl Ether → 2-Ethyl-4-(hydroxymethyl)phenol

HRID 1269663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269663
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=[O:7])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC>C1COCC1>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:8]=[CH:9][C:10]=1[OH:11])[CH3:2]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 220387133-Ethyl-4-hydroxybenzaldehyde

Produkt 1

HCID 220112042-Ethyl-4-(hydroxymethyl)phenolAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-ethyl-4-hydroxybenzaldehyde (4.7 g, 26 mmol) in anhydrous THF (150 mL) at 0° C. under N2 was added dropwise 1 M LiAlH4 in Et2O (52 mL, 52.2 mmol). The resulting mixture was stirred at 0° C. for 2 h and then quenched by cautious addition of water and stirred for 15 minutes. The reaction mixture was then absorbed onto silica and loaded onto a silica pad which was washed with EtOAc. The EtOAc washings were collected and concentrated in vacuo to afford the title compound as a colourless oil (3.67 g).

Aufarbeitung

  1. customquenched by cautious addition of water
  2. stirringstirred for 15 minutes
  3. customThe reaction mixture was then absorbed onto silica
  4. washwas washed with EtOAc
  5. customThe EtOAc washings were collected
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8c2e015437b54ae2bf465a8aefff7d9c
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

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