Sodium Hydroxide → 4,4-Dimethylpentanoic acid

HRID 15283

Reaktionsgleichung

Reaktionsgleichung von HRID 15283
C[O:2][C:3](=[O:10])[CH2:4][CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7].[OH-].[Na+]>O.C(Cl)Cl>[CH3:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH2:4][C:3]([OH:10])=[O:2]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 126561444,4-Dimethyl-pentanoic acid methyl ester

Produkt 1

HCID 142374,4-Dimethylpentanoic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4,4-Dimethyl-pentanoic acid methyl ester (7.0 g, 48.5 mmol, 1.0 eq.) was treated with a solution of NaOH (4.0 g, 100 mmol, 2.1 eq.) in water (5 mL). The homogeneous solution was allowed to stir for 4-5 hours. The reaction was diluted with CH2Cl2 and the aqueous layer was extracted with CH2Cl2 (50 mL×3). The aqueous layer was acidified with 6M HCl to pH˜1.5 and extracted with ethyl acetate (50 mL×3). The combined ethyl acetate fractions were dried over MgSO4, filtered and evaporated to provide 4,4-dimethyl-pentanoic acid (5.35 g, 41.1 mmol, 85%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 0.89 (s, 9H), 1.53-1.57 (m, 2H), 2.26-2.30 (m, 2H).

Aufarbeitung

  1. extractionthe aqueous layer was extracted with CH2Cl2 (50 mL×3)
  2. extractionextracted with ethyl acetate (50 mL×3)
  3. dry with materialThe combined ethyl acetate fractions were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-716e3510a0784031b618357edaf011b3
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732449B2

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