Sulfuric Acid → 2,4-Dihydroxy benzoic acid tert-butyl ester

HRID 18438

Reaktionsgleichung

Reaktionsgleichung von HRID 18438
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH2:17]=[C:18]([CH3:20])[CH3:19].C([O-])(O)=O.[Na+]>O1CCOCC1>[C:18]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:2]=1[OH:1])([CH3:20])([CH3:19])[CH3:17]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 14912,4-Dihydroxybenzoic AcidHCID 8255IsobutyleneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 217835472,4-Dihydroxy benzoic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

To a solution of 2,4-dihydroxy benzoic acid (3.08 g; 20 mmol) in dioxane (50 mL) was added conc. H2SO4 (3 mL) and the solution was cooled to −50° C. Isobutene (40 g) was added, the reaction flask sealed and allowed to warm to room temperature. The reaction mixture was stirred overnight, cooled to −30° C. and pH adjusted to 8 using saturated NaHCO3 (aq). The organic phase was Isolated, dried, evaporated to dryness and purified by column chromatography (SiO2-heptane/EtOAc=4:1) to yield 2.3 g (54%). MS (LC-MS): 209 (MH−).

Aufarbeitung

  1. customthe reaction flask sealed
  2. temperatureto warm to room temperature
  3. temperaturecooled to −30° C.
  4. customThe organic phase was Isolated
  5. customdried
  6. customevaporated to dryness
  7. custompurified by column chromatography (SiO2-heptane/EtOAc=4:1)
  8. customto yield 2.3 g (54%)

Quellen und Nachweise

ORD-Eintrag
ord-4671f261620a43e7a6758dd6c1540ef9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741352B2

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