(+-)-4-Hydroxymandelic acid → Benzeneacetic acid, alpha,4-dihydroxy-, ethyl ester

HRID 1071777

Reaktionsgleichung

Reaktionsgleichung von HRID 1071777
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[C:13]1(C)C=CC(S(O)(=O)=O)=C[CH:14]=1.C([O-])(O)=O.[Na+]>C(O)C.O>[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7]([O:9][CH2:13][CH3:14])=[O:8])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 328(+-)-4-Hydroxymandelic acidHCID 6101p-Toluenesulfonic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 111357Benzeneacetic acid, alpha,4-dihydroxy-, ethyl esterAusbeute 288 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 5 g of 4-hydroxymandelic acid and 1.28 g of p-toluenesulfonic acid in 200 ml of ethanol is heated at 50° C. for 4 hours. The mixture is poured into saturated aqueous NaHCO3 solution, and a white precipitate is formed. The mixture is diluted with water until the precipitate disintegrates, and then is extracted with diethyl ether. The organic phases are dried over sodium sulfate. Filtration and evaporation of the solvent give ethyl 4-hydroxymandelate (4.2 g, 82%) as a pale yellowish solid.

Aufarbeitung

  1. customa white precipitate is formed
  2. extractionis extracted with diethyl ether
  3. dry with materialThe organic phases are dried over sodium sulfate
  4. filtrationFiltration and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-483957f9c4454e988f199e2119f4489a
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906113B2

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