[C:1]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:9]=2[CH:10]=1)(=O)[CH2:2][CH2:3][CH3:4].NN.C(O)COCCO.[OH-].[K+]>O>[CH2:1]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:9]=2[CH:10]=1)[CH2:2][CH2:3][CH3:4]A mixture of 31.5 g. (0.14 mol.) of 2-butyryl-5-chlorobenzofuran and 35 ml. of 98% hydrazine in 70 ml. of diethylene glycol was warmed for a few minutes on a steam bath. Then 23.3 g. of potassium hydroxide was added and the reaction mixture was refluxed for two hours. After cooling, water was added to the mixture and the resulting aqueous solution was extracted with benzene. The extract was washed with water, 10% aqueous hydrochloric acid and water, dried (MgSO4) and concentrated in vacuo to yield 2-n-butyl-5-chlorobenzofuran, b.p. 70°-75° (10-15 mm.).
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