Sulfuric Acid → Cyclopropyl(4-hydroxyphenyl)methanone
Reaktionsgleichung
ClCC[CH2:4][C:5]1(O)[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH2:6]1.[OH-:14].[Na+].S(=O)(=O)(O)O.C([O:24][CH2:25][CH3:26])(=O)C>>[CH:9]1([C:10]([C:5]2[CH:4]=[CH:26][C:25]([OH:24])=[CH:7][CH:6]=2)=[O:14])[CH2:8][CH2:11]1Komponenten
5
Versuchsvorschrift
4-Chloropropyl(4-hydroxyphenyl)methanone (25.1 g, 127 mmol) was added to a 2 N aqueous solution of sodium hydroxide (283 mL, 566 mmol) in several portions under ice cooling. The reaction mixture was allowed to warm up to room temperature, and was stirred for 6 hours, and then dilute sulfuric acid (1.8 N) was added to the reaction mixture under ice cooling until a pH value of 2 was obtained. The reaction mixture was subjected to extraction twice with ethyl acetate. The organic layer thus obtained was washed with water and brine, and then was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1, v/v) to give the title compound (17.7 g, yield: 86%).