Hydrochloric Acid → Methyl 2-(1-hydroxyethyl)-3-phenylpropionate

HRID 248711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 248711
[C:1]([CH:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:3])[CH3:2].[BH4-].[Na+].Cl>CO>[OH:3][CH:1]([CH:4]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10679785Methyl 2-benzyl-3-oxobutanoate

Produkt 1

HCID 15670376Methyl 2-(1-hydroxyethyl)-3-phenylpropionateAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Methyl 2-acetyl-3-phenylpropionate (60 g) is dissolved in methanol (300 ml), and thereto is added portionwise sodium boro hydride (2.9 g) with stirring under ice cooling, and the mixture is stirred under ice cooling from 2 hours. The reaction mixture is adjusted to pH 1 with 10% hydrochloric acid, and methanol is distilled off under reduced pressure. The residue is extracted with ethyl acetate. The extract is washed with diluted aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and ethyl acetate is distilled off under reduced pressure to give methyl 2-(1-hydroxyethyl)-3-phenylpropionate (60.4 g). IR (film; cm-1): 3400 (broad), 1730

Aufarbeitung

  1. stirringthe mixture is stirred under ice cooling from 2 hours
  2. distillationis distilled off under reduced pressure
  3. extractionThe residue is extracted with ethyl acetate
  4. washThe extract is washed with diluted aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate, and ethyl acetate
  6. distillationis distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f0bca72d51944786b05d950898fb42bf
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05210266

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