Tyrosol → Tert-butyl [4-(2-hydroxyethyl)phenoxy]acetate

Reaktionsgleichung

[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>C(#N)C>[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:6][CH:5]=1

Komponenten

Versuchsvorschrift

A mixture of 4-(2-hydroxyethyl)phenol (3.8 ml, 25.834 mmol) was dissolved in acetonitrile (25 ml), potassium carbonate (7.085 g, 51.267 mmol) and tert-butyl bromoacetate (5.000 g, 25.834 mmol) was boiled under reflux for 16 hours. The solvent was evaporated under reduced pressure. The residue was dissolved in EtOAc and washed with brine and water, dried with MgSO4 and evaporated under reduced pressure to give the desired product was obtained (6.00 g, yield 92.8%).