Glyoxylic Acid → 3-Ethoxy-4-hydroxymandelic acid

HRID 1013563

Reaktionsgleichung

Reaktionsgleichung von HRID 1013563
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH3:2].[C:11]([OH:15])(=[O:14])[CH:12]=[O:13].[OH-].[Na+]>O>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH:12]([OH:13])[C:11]([OH:15])=[O:14])[CH:7]=[CH:6][C:5]=1[OH:10])[CH3:2]

Komponenten

5

Edukt 3

HCID 760Glyoxylic AcidHCID 14798Sodium HydroxideHCID 667552-Ethoxyphenol

Produkt 1

HCID 1937923-Ethoxy-4-hydroxymandelic acidAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2-Ethoxyphenol (56.6, 0.401 mol, 1 eq.), glyoxylic acid (50% aqueous solution) (41.0 mL, 0.396 mol, 0.99 eq.), and distilled water (110 mL) were combined. The mixture was cooled in an ice bath, and a solution of 10% NaOH (32.2 g NaOH in 300 mL distilled water, 0.805 mol, 2 eq.) was slowly added via addition funnel. The reaction was allowed to slowly warm to room temperature, and after ˜18 hours, the solution was washed with ethyl acetate (4×250 mL), then acidified with 6N HCl until pH ˜3. NaCl was added and the product was then extracted into ethyl acetate (4×200 mL). The organic phase was washed with brine, dried over magnesium sulfate, and solvent was removed under vacuum, giving 51.8 g of intermediate 2 as a light pink solid.

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice bath
  2. washthe solution was washed with ethyl acetate (4×250 mL)
  3. additionNaCl was added
  4. extractionthe product was then extracted into ethyl acetate (4×200 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate, and solvent
  7. customwas removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3b66a167e7a04ae38c6bd9418908d26d
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981931B2

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