Water → 4-(tert-Butoxycarbonyl)benzoic acid

HRID 2253627

Reaktionsgleichung

Reaktionsgleichung von HRID 2253627
[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:19]=[CH:18][C:10]([C:11]([O:13]C(C)(C)C)=[O:12])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].O>C(O)(C)(C)C>[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:18][CH:19]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 316007Di-t-butyl terephthalate

Produkt 1

HCID 27609544-(tert-Butoxycarbonyl)benzoic acidAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A slurry of terephthalic acid di-tert-butyl ester (6.1 g, 0.022 mole) in tert-butanol (30 mL) was added to 1N KOH (22 mL, 0.022 mole). The mixture was heated to 60° C. for 7-8 hours. After cooling the mixture was treated with water and extracted 3 times with ethyl acetate. The aqueous layer was acidified with diulute HCL and the product was extracted into ethyl acetate. After washing of the organic layer with a saturated aqueous NaCl solution and drying over MgSO4, the solvent was filtered and concentrated to yield terephthalic acid mono tert-butyl ester as a white solid (4.7 g, 96%) melting at 100°-102° C.

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. extractionextracted 3 times with ethyl acetate
  3. extractionthe product was extracted into ethyl acetate
  4. washAfter washing of the organic layer with a saturated aqueous NaCl solution
  5. dry with materialdrying over MgSO4
  6. filtrationthe solvent was filtered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-21d925bf4fbd4885bbeb786503ddc2ec
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05232928

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