Reaktion #46716

Reaktionsgleichung

NaHCO3

Isobutene

2,4-dihydroxy benzoic acid

H2SO4

→

2,4-Dihydroxy benzoic acid tert-butyl ester

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction flask sealed
2. 2
   Temperaturto warm to room temperature
3. 3
   Temperaturcooled to −30° C.
4. 4
   SonstigeThe organic phase was Isolated
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated to dryness
7. 7
   Sonstigepurified by column chromatography (SiO2-heptane/EtOAc=4:1)
8. 8
   Sonstigeto yield 2.3 g (54%)

Vorschrift

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−).

Quelle