Phenol → 2-Phenoxy-1-formyl-1-cyclopentene

Reaktionsgleichung

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

Komponenten

Versuchsvorschrift

To a solution of residue (100 g, 0.77 mol) obtained in example 1 in acetone (400 mL), phenol (79.3 g, 0.84 mol) and K2CO3 (126.8 g, 0.92 mol) were added. The mixture was stirred under nitrogen for 12 hours at room temperature and monitored by TLC (petroleum ether/ethyl acetate=10:1). After the reaction completed, the solvent was removed on a rotary evaporator, and water (300 mL) was added. The mixture was extracted with EtOAc (2×100 mL). The organic layer was washed with aqueous sodium carbonate (2×50 mL) and water (50 mL). After dried over sodium sulfate, the solvent was removed and 2-phenoxy-1-formyl-1-cyclopentene was obtained (155 g, contains some phenol), which was used directly in the next step.