Hydrochloric Acid → Seratrodast

HRID 2254351

Reaktionsgleichung

Reaktionsgleichung von HRID 2254351
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[CH:11]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].Cl.[OH2:27]>C(#N)C.N.N(S([O-])(=O)=O)(S([O-])(=O)=O)[O].[K+].[K+]>[CH3:10][C:4]1[C:5](=[O:27])[C:6]([CH3:9])=[C:7]([CH3:8])[C:2](=[O:1])[C:3]=1[CH:11]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 145139667-(2-Hydroxy-3,4,6-trimethylphenyl)-7-phenylheptanoic acid

Produkt 1

HCID 2449SeratrodastAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 222AmmoniaLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 3032624Potassium nitrosodisulfonateLösungsmittel

Versuchsvorschrift

7-(2-hydroxy-3,4,6-trimethylphenyl)-7-phenylheptanoic acid (5.0 g) was dissolved in a mixed solution of acetonitrile (25 ml), water (10 ml) and 25% aqueous ammonia (1 ml), to which 3% aqueous solution (280 ml) of potassium nitrosodisulfonate (Fremy's salt) was added. The mixture was stirred at a temperature of 2° to 4° C. for 2 hours. The reaction mixture was acidified with hydrochloric acid, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water twice. Ethyl acetate was distilled off under reduced pressure, and the residue was recrystalized from a mixed solution of acetonitrile and water (6:4) to give 7-(3,5,6-trimethyl-1,4-benzoquinone-2-yl)-7-phenylheptanoic acid (4.90 g, 94.1%) as yellow crystals.

Aufarbeitung

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water twice
  4. distillationEthyl acetate was distilled off under reduced pressure
  5. customthe residue was recrystalized from a mixed solution of acetonitrile and water (6:4)

Quellen und Nachweise

ORD-Eintrag
ord-f36bdf47dde04005bcac95d3661a57ff
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05235091

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