Methyl 3-(2-hydroxyethyl)benzoate → 2-Methylpentane

HRID 1689239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689239
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13](OC)=[O:14]>O1CCCC1>[CH3:13][CH2:12][CH2:11][CH:10]([CH3:19])[CH3:9].[OH:14][CH2:13][C:12]1[CH:11]=[C:10]([CH2:9][CH2:8][OH:7])[CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 2

HCID 10535371Methyl 3-(2-hydroxyethyl)benzoateHCID 21226445Aluminium lithium hydride

Produkt 2

HCID 78922-MethylpentaneHCID 579891802-(3-(Hydroxymethyl)phenyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium aluminum hydride (1M in diethyl ether, 5.55 mL) was added dropwise over 5 min to a stirred solution of methyl 3-(2-hydroxyethyl)benzoate (1.0 g) in tetrahydrofuran (15 mL) cooled in an ice bath. After 1 h, the reaction mixture was quenched with methanol and evaporated in vacuo. Purification was by silica gel chromatography eluting with ethyl acetate:isohexane, 2:1, then ethyl acetate to give the subtitled compound as a gum. Yield 0.5 g.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customthe reaction mixture was quenched with methanol
  3. customevaporated in vacuo
  4. customPurification
  5. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-efec3a709c1e4a5180a85bf235d153c7
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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