Acetone → 4-Benzyloxy-3-(1-phenyl-vinyl)-benzoic acid-methylester

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH2:12])[CH:5]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CC(C)=O>>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:6]([C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH2:12])[CH:5]=1

Komponenten

Edukt 3

HCID 180Acetone

HCID 7498Benzyl Bromide

HCID 226484304-Hydroxy-3-(1-phenyl-vinyl)-benzoic acid methylester

Produkt 1

HCID 226484274-Benzyloxy-3-(1-phenyl-vinyl)-benzoic acid-methylesterAusbeute 80 %

Versuchsvorschrift

To a solution of 1.50 g (5.9 mmole) 4-hydroxy-3-(1-phenyl-vinyl)-benzoic acid methylester and 1.04 g (6.1 mmole) benzyl bromide in 10 ml abs. acetone 1.24 g (8.9 mmole) potassium carbonate are added. The reaction mixture is then heated for 4 hours with recycling. Following cooling of the suspension, it is filtered and the residue is washed with 50 ml diethtylether. The solvent is removed and the raw product obtained is cleaned by column chromatography (silica gel, petroleum ether/MTBE=5/1 (v/v)). 1.62 g (4.7 mmole, 80%) 4-benzyloxy-3-(1-phenyl-vinyl)-benzoic acid-methylester are obtained.