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

HRID 471008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471008
[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-72fa00a451f64cdcb4b4147b37c97ab2
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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