Lithium Hydroxide → 6-(Tert-butoxy)-6-oxohexanoic acid

HRID 331540

Reaktionsgleichung

Reaktionsgleichung von HRID 331540
[OH-].[Li+].C[O:4][C:5](=[O:17])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]>CO.O>[C:13]([O:12][C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:17])=[O:4])([CH3:16])([CH3:14])[CH3:15]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 184750351-(1,1-Dimethylethyl) 6-methyl hexanedioate

Produkt 1

HCID 159089376-(Tert-butoxy)-6-oxohexanoic acidAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

Lithium hydroxide (0.53 g, 22 mmol) was added to a solution of hexanedioic acid tert-butyl ester methyl ester (4.8 g, 22 mmol) in 3:1 methanol-water (80 mL), and the resulting mixture was stirred at room temperature for 16 hours. The mixture was evaporated under vacuum. The residue was partitioned between water (60 mL) and methylene chloride (75 mL), and the aqueous phase was washed with methylene chloride (3×75 mL) and evaporated, providing 4.0 g of hexanedioic acid mono-tert-butyl ester, lithium salt; 1H NMR (D2O) δ 1.45 (s, 9H), 1.54-1.58 (m, 4H), 2.15-2.20 (m, 2H), 2.25-2.34 (m, 2H).

Aufarbeitung

  1. customThe mixture was evaporated under vacuum
  2. customThe residue was partitioned between water (60 mL) and methylene chloride (75 mL)
  3. washthe aqueous phase was washed with methylene chloride (3×75 mL)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0c8b0c57370c4c28afc7cb9d2a04bc14
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877780B2

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