Reaktion #47657

Reaktionsgleichung

methyl magnesium bromide

ethyl acetate

hydrochloric acid

1-(4-hydroxy-phenyl)-propan-2-one

→

4-(2-hydroxy-2-methyl-propyl)-phenol

Ausbeute 77.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic phase was separated
2. 2
   Einengenconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in a small volume of tetrahydrofuran
4. 4
   workup.ADDITIONthe mixture was treated with an excess of hexanes

Vorschrift

To a solution of methyl magnesium bromide (3 M, 14 mL, 39.94 mmol) cooled to 0° C. was added tetrahydrofuran (10 mL) and as solution of 1-(4-hydroxy-phenyl)-propan-2-one (1 g, 6.66 mmol) in tetrahydrofuran (30 mL). The resulting mixture was then warmed to room temperature and then stirred for 2 h. At this time, the reaction was partioned between ethyl acetate and water. The water layer was made acidic with 1N aqueous hydrochloric acid (pH=1). The organic phase was separated and concentrated in vacuo. The residue was dissolved in a small volume of tetrahydrofuran and the mixture was treated with an excess of hexanes. This resulted in the precipitation of the product 4-(2-hydroxy-2-methyl-propyl)-phenol (0.85 g, 77%) as a white solid.

Quelle