Water → (7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

Reaktionsgleichung

C([O:3][C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:12][CH:13]1[CH2:15][O:14]1)=O.[OH-].[K+].[OH-].[Na+].O>O1CCOCC1.CCOC(C)=O>[Br:10][C:8]1[CH:7]=[CH:6][C:5]2[O:11][CH2:12][CH:13]([CH2:15][OH:14])[O:3][C:4]=2[CH:9]=1

Komponenten

Edukt 4

HCID 962Water

HCID 14797Potassium Hydroxide

HCID 14798Sodium Hydroxide

HCID 212210275-Bromo-2-(oxiran-2-ylmethoxy)phenyl formate

Produkt 1

HCID 233965(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanolAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

Versuchsvorschrift

5-bromo-2-(oxiran-2-ylmethoxy)phenyl formate (12.6 g, 46.0 mmol) was dissolved in dioxane (50 ml) and KOH (10%)/NaOH (20%) was added. Water and EtOAc was added and the phases were separated. The combined organic phases were washed with brine and dried to give the title compound (10.3 g). MS m/z (rel. intensity, 70 eV) 245 (M+, 96) 244 (M+, bp), 213 (29), 189 (46), 188 (49).