alpha-Ethynylbenzenemethanol → 3-Oxo-3-phenylpropyne
反応式
[C:1]1([CH:7]([OH:10])[C:8]#[CH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(C)=O.O.S(=O)(=O)(O)O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]1([C:7]([C:8]#[CH:9])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1参加物
6
実験手順
A solution of 1-phenyl-2-propyne-1-ol (34.2 g) in 50 ml acetone is cooled down to 0°, stirred under N2 and treated dropwise, over a period of 3 hours with a solution of chromium trioxide (17.5 g) in water (50 ml) and concentrated sulfuric acid (14.8 ml), keeping the temperature below 5° at all times. After the addition is complete, the mixture is stirred for another hour at 5°. The reaction mixture is then diluted with water (100 ml) and extracted with two 250-ml portions of ether. The organic extracts are combined, dried over anhydrous sodium sulfate, filtered and stripped to give a yellow product. A small amount dried on a porous plate gives a m.p. of 45°-47°.