Reaktion #568613

Reaktionsgleichung

MgSO4

NaOH

NaOH

product

methyl 3-(3,4-dichlorophenyl)-2-propenoate

Dibal-H

→

3-(3,4-dichlorophenyl)-2-propene-1-ol

Ausbeute 100.0%

Lösungsmittel

Et2O

Et2O

water

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGStir for 5 min
2. 2
   SonstigeRemove the aluminum salts
3. 3
   Filtrationby filtration through a course glass frit
4. 4
   WaschenWash the solids with Et2O (1 L)
5. 5
   Einengenconcentrate the filtrate in vacuo

Vorschrift

Treat a solution of the product of Step 1 (15 g, 65 mmol) in dry THF (250 mL), kept cool in a large ambient temperature water bath, with Dibal-H (140 mL, 140 mmol, 2.15 eq) over 30 min. Stir the resulting solution for 30 min at 23° C., pour into Et2O (500 mL), treat with water (5 mL), 15% NaOH (5 mL) and water (15 mL). Stir for 5 min, dilute the mixture with Et2O (200 mL) and treat with 15% NaOH (15 mL). Add MgSO4 to cause a colorless precipitate. Remove the aluminum salts by filtration through a course glass frit. Wash the solids with Et2O (1 L) and concentrate the filtrate in vacuo to give 13.2 g (65 mmol, 99%) of 3-(3,4-dichlorophenyl)-2-propene-1-ol as an off-white solid.

Quelle