Reaktion #54149

ord-d467a35bd360402fa8a4d28a0921cce1

Reaktionsgleichung

CC(Oc1ccc(O)c2ccccc12)C(=O)O
2-(4-hydroxy-1-naphthoxy)propionic acid
O=P([O-])(O)O.[K+]
potassium dihydrogen phosphate
[K+].[K+].[O]N(S(=O)(=O)[O-])S(=O)(=O)[O-]
potassium nitrosodisulfonate
→
CC(OC1=CC(=O)C(=O)c2ccccc21)C(=O)O
4-(1-Carboxyethoxy)-1,2-naphthoquinone

Edukte

CC(Oc1ccc(O)c2ccccc12)C(=O)O
2-(4-hydroxy-1-naphthoxy)propionic acid
O=P([O-])(O)O.[K+]
potassium dihydrogen phosphate
[K+].[K+].[O]N(S(=O)(=O)[O-])S(=O)(=O)[O-]
potassium nitrosodisulfonate

Reagenzien

Keine

Lösungsmittel

CCO
ethanol
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe yellow-brown solid was collected
  2. 2
    Waschenwashed with a litter water
  3. 3
    Sonstigedried (under nitrogen)

Vorschrift

To a solution of 38.0 g potassium dihydrogen phosphate in 7.5 l of distilled water (pH 4.0) was added 89.4 g (0.33 mol) potassium nitrosodisulfonate (Fremy's reagent). To this solution was added immediately a solution of 34.8 g (0.15 mol) of 2-(4-hydroxy-1-naphthoxy)propionic acid in 125 ml ethanol. The mixture was stirred for 2.5 hours under nitrogen at room temperature. The yellow-brown solid was collected, washed with a litter water and dried (under nitrogen). The yield was 30.0 g (81 percent). The crude product melted at 182° to 184° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04147544uspto-grants-1979_04