L-Malic Acid → (S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

HRID 82493

Reaktionsgleichung

Reaktionsgleichung von HRID 82493
[CH2:1]([C:7]([OH:9])=[O:8])[C@H:2]([OH:6])[C:3]([OH:5])=[O:4].[CH3:10][C:11]1C=CC(S([O-])(=O)=O)=C[CH:12]=1.C1C=C[NH+]=CC=1>COC(OC)(C)C>[CH3:10][C:11]1([CH3:12])[O:6][C@@H:2]([CH2:1][C:7]([OH:9])=[O:8])[C:3](=[O:5])[O:4]1

Komponenten

4

Edukt 2

HCID 222656L-Malic AcidHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Produkt 1

HCID 641720(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acidAusbeute 2.850,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 64952,2-DimethoxypropaneLösungsmittel

Versuchsvorschrift

To a suspension of L-(−)-Malic acid (100.0 g, 0.74 mol) in 2,2-dimethoxy propane (200 mL) was added PPTS (2.60 g, 15.11 mmol) at room temperature (25° C.). The reaction mixture stirred at same temperature over a period of 48 h. The resulting mixture was partitioned between water (1.0 L) and dichloromethane (2.5 L), the aqueous layer was extracted twice with dichloromethane (2×500 mL). The combined organic layers dried (Na2SO4) and concentrated under reduced pressure to obtain colourless solid (75.0 g, 58%).

Aufarbeitung

  1. customThe resulting mixture was partitioned between water (1.0 L) and dichloromethane (2.5 L)
  2. extractionthe aqueous layer was extracted twice with dichloromethane (2×500 mL)
  3. dry with materialThe combined organic layers dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-70fba1f07a044c60b547eba90c85a317
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846721B2

Verknüpfte Notizen

Wird geladen…