Sodium Iodide → 4-Hydroxy-2,2-dimethyl-butyric acid benzyl ester

HRID 1806916

Reaktionsgleichung

Reaktionsgleichung von HRID 1806916
[K+].[OH:2][CH2:3][CH2:4][C:5]([CH3:10])([CH3:9])[C:6]([O-:8])=[O:7].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>>[CH2:11]([O:7][C:6](=[O:8])[C:5]([CH3:10])([CH3:9])[CH2:4][CH2:3][OH:2])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 23712640Potassium 4-hydroxy-2,2-dimethylbutyrate

Produkt 1

HCID 141523044-Hydroxy-2,2-dimethyl-butyric acid benzyl esterAusbeute 67,5 %

Versuchsvorschrift

Step B To the mixture of 4-hydroxy-2,2-dimethyl-butanoic acid monopotassium salt (60 mmol) and benzyl bromide (8.55 mL, 72 mmol) were added NaI (10.8 g, 72 mmol) and K2CO3 (8.29 g, 60 mmol). The reaction mixture was stirred at reflux for 18 h. The precipitate was filtered off and the filtrate was evaporated. The residue was purified by flash column chromatography (EtOAc: hexanes=1:2) to give 4-hydroxy-2,2-dimethyl-butyric acid benzyl ester as a colorless oil (9 g, 67%)

Aufarbeitung

  1. temperatureat reflux for 18 h
  2. filtrationThe precipitate was filtered off
  3. customthe filtrate was evaporated
  4. customThe residue was purified by flash column chromatography (EtOAc: hexanes=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-f77f9c1b10e94db7b4985ebd4eafe25c
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354444B2

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