Reaktion #47650

Reaktionsgleichung

hydrochloric acid

methyl magnesium bromide

ethyl acetate

(3-hydroxy-phenyl)-acetic acid methyl ester

→

3-(2-hydroxy-2-methyl-propyl)-phenol

Ausbeute 100.0%

Lösungsmittel

water

water

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted twice with ethyl acetate
2. 2
   TrocknenThe combined organic phases were dried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo which

Vorschrift

To a solution of methyl magnesium bromide (3 M, 12 mL, 36.06 mmol) cooled to 0° C. was added tetrahydrofuran (10 mL) and (3-hydroxy-phenyl)-acetic acid methyl ester (1 g, 6.01 mmol) as a solution in tetrahydrofuran (5 mL). The resulting mixture was warmed to room temperature stirred for 30 min and then poured carefully into a biphasic mixture of ethyl acetate and water. The water layer was made acidic (pH=1) with 1N aqueous hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo which afforded 3-(2-hydroxy-2-methyl-propyl)-phenol (1 g, 100%) as a white solid.

Quelle