Methyl 5-(benzyloxy)-2-hydroxybenzoate → 4-(Benzyloxy)-2-(hydroxymethyl)phenol

HRID 1521

Reaktionsgleichung

Reaktionsgleichung von HRID 1521
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][C:11]=1[OH:24]>O1CCCC1>[CH2:17]([O:16][C:14]1[CH:13]=[CH:12][C:11]([OH:24])=[C:10]([CH2:9][OH:8])[CH:15]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

4

Edukt 2

HCID 13026913Methyl 5-(benzyloxy)-2-hydroxybenzoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 196909214-(Benzyloxy)-2-(hydroxymethyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Lithium aluminium hydride (0.235 g, 6.2 mMol) was suspended in tetrahydrofuran (25 ml) and cooled to 0° C. 5-Benzyloxy-2-hydroxy benzoic acid methyl ester (2 g, 7.75 mMol) in tetrahydrofuran (10 ml) was added dropwise, via cannula. The mixture was warmed to room temperature and stirred for 20 minutes. The reaction was then cooled to 0° C. and cautiously quenched by the addition of water (0.5 ml), 2M sodium hydroxide solution (0.5 ml), and water (1 ml). The resulting mixture was stirred at room temperature for 30 minutes and filtered. The filtrate was evaporated in vacuo to yield 4-benzyloxy-2-hydroxymethyl phenol as a clear oil which was used in the next step without further purification.

Aufarbeitung

  1. temperatureThe mixture was warmed to room temperature
  2. temperatureThe reaction was then cooled to 0° C.
  3. customcautiously quenched by the addition of water (0.5 ml), 2M sodium hydroxide solution (0.5 ml), and water (1 ml)
  4. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d01bdcbca7ae4670b375df3584280165
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726165

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