Triethyl Citrate → Diethyl Citrate

HRID 743718

Reaktionsgleichung

Reaktionsgleichung von HRID 743718
[C:1]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:2][C:3]([CH2:10][C:11]([O:13]CC)=[O:12])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[OH:4].[OH-].[Na+]>C(O)C.O>[OH:4][C:3]([C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH2:2][C:1]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][C:11]([OH:13])=[O:12]

Komponenten

5

Edukt 2

HCID 6506Triethyl CitrateHCID 14798Sodium Hydroxide

Produkt 1

HCID 15384083Diethyl CitrateAusbeute 28,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of triethyl citrate (34.1 g, 123 mmol) in ethanol and water (30 ml) is treated with sodium hydroxide (3.70 g, 92.6 mmol) and stirred at room temperature under argon for 4.5 hours. The reaction mixture is concentrated on a rotary evaporator then diluted with water (50 ml). The pH is adjusted to ca. 1 using 2N HCl. The aqueous solution is then extracted with a large excess of chloroform (4×150 ml). The combined organic layers are dried (MgSO4), filtered and concentrated to give crude oil. Purification by flash chromatography (5% MeOH/CH2Cl2 to 1% AcOH/5%MeOH/CH2Cl2) gives 8.72 g of product (38% as a racemate.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated on a rotary evaporator
  2. additionthen diluted with water (50 ml)
  3. extractionThe aqueous solution is then extracted with a large excess of chloroform (4×150 ml)
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude oil
  8. customPurification by flash chromatography (5% MeOH/CH2Cl2 to 1% AcOH/5%MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-411ed25710a04d778d1ae23090065934
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556990

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