Hydrochloric Acid → 4-Hydroxyphthalic acid

HRID 1052937

Reaktionsgleichung

Reaktionsgleichung von HRID 1052937
[OH-:1].[Na+].S([C:7]1[CH:8]=[C:9]([C:16]([OH:18])=[O:17])[C:10](=[CH:14][CH:15]=1)[C:11]([OH:13])=[O:12])(O)(=O)=O.Cl>O>[OH:1][C:7]1[CH:8]=[C:9]([C:16]([OH:18])=[O:17])[C:10](=[CH:14][CH:15]=1)[C:11]([OH:13])=[O:12]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 69624-Sulfophthalic acidHCID 14798Sodium Hydroxide2×

Produkt 1

HCID 118814-Hydroxyphthalic acidAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

Sodium hydroxide (251.9 g, 6.30 mol) was added in portions to 4-sulphophthalic acid (50% in water, 258.4 g, 0.525 mol) in a steel vessel accompanied by stirring. After the addition of approx. one third NaOH the increasingly more viscous mixture was heated to 180° C. Once the addition had ended the mixture was stirred for a further 2 h at 200° C. During cooling, the residue was dissolved in water (1000 ml). Conc. hydrochloric acid (620 ml, pH=1) was added accompanied by ice cooling. The solution was extracted with ethyl acetate (5×400 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated on the rotary evaporator. The slightly yellow solid was recrystallized from ethyl acetate. 68.64 g (0.377 mol; 72% yield) of a white solid was obtained.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureincreasingly more viscous mixture
  3. additionOnce the addition
  4. stirringwas stirred for a further 2 h at 200° C
  5. temperatureDuring cooling
  6. extractionThe solution was extracted with ethyl acetate (5×400 ml)
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated on the rotary evaporator
  10. customThe slightly yellow solid was recrystallized from ethyl acetate
  11. custom68.64 g (0.377 mol; 72% yield) of a white solid was obtained

Quellen und Nachweise

ORD-Eintrag
ord-e78c004b9e3548b7adb0dc5ce663f69f
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09393181B2

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