Water → Benzyl 3-hydroxy-2,2-dimethylpropanoate

HRID 729595

Reaktionsgleichung

Reaktionsgleichung von HRID 729595
[OH-].[K+].O[C:4]([CH3:10])([CH2:8][OH:9])[C:5]([OH:7])=[O:6].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.[CH3:20]N(C=O)C>C(OCC)(=O)C>[CH2:11]([O:7][C:5](=[O:6])[C:4]([CH3:10])([CH3:20])[CH2:8][OH:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 5

HCID 962WaterHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 5607812-Methylglyceric acid

Produkt 1

HCID 18922595Benzyl 3-hydroxy-2,2-dimethylpropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Add potassium hydroxide (486.7 mmol, 32.1 g) over a solution of 2,3-dihydroxy-2-methyl-propionic acid (423.2 mmol, 50 g) in 300 mL of DMF. Stir for 1 hour at 100° C. Then add benzyl bromide (584.04 mmol, 69.46 mL) and stir overnight. Cool down the mixture and dilute with ethyl acetate. Wash organic layer with water. Wash aqueous layer with ethyl acetate several times. Combine organic layers and dry over sodium sulfate, filter and concentrate under reduced pressure. 1H NMR (CDCl3, 300 MHz): δ ppm :7.36-7.32 (m, 5H), 5.1 (s, 2H), 3.5 (s, 2H), 1.21 (s, 6H).

Aufarbeitung

  1. temperatureCool down the mixture
  2. dry with materialCombine organic layers and dry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dbc2e2a6b2624307b2c09ace19340ad6
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582638B2

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