ethyl 2-(2-ethoxycarbonylphenyl)benzoate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 3 g LiAlH4 was added 100 ml anhydrous ethyl ether. While cooling with ice-bath and stirring intensely, 0.05 mol diethyl 2,2′-biphenyldicarboxylate was slowly added dropwise. The reaction mixture was heated refluxing for 5 hours, then cooled. Excess LiAlH4 was decomposed with water. The mixture was filtered, and the filtrate was extracted with ethyl ether. The extract was dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 2,2′-biphenyldimethanol as a white solid, the yield was 75%, and m.p. was 98-103° C. IR spectrum had a strong absorption peak at 3400 cm−1, and had no absorption peak at about 1700 cm−1. This demonstrated that the reduction reaction was carried out completely. While cooling with ice-bath The reaction mixture was heated refluxing for 5 hours cooled The mixture was filtered the filtrate was extracted with ethyl ether The extract was dried over anhydrous sodium sulfate The solvent was removed

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 0.1 mol 2,2′-biphenyl dicarboxylic acid anhydride were added 0.3 mol ethanol, 40 ml toluene, and 0.4 ml concentrated sulfuric acid with stirring. Then the reaction mixture was heated refluxing and the water produced was removed by using a water separator until the amount of the water separated reached theoretical value. Upon the reaction completion, the mixture was neutralized with saturated sodium carbonate solution and extracted with ethyl acetate. The upper layer was separated, washed with saturated saline to neutrality, and dried over anhydrous sodium sulfate. The solvent was removed. Distillation under reduced pressure gave diethyl 2,2′-biphenyldicarboxylate as a colorless liquid, and the yield was 90%. Then the reaction mixture was heated refluxing was removed separated extracted with ethyl acetate The upper layer was separated washed with saturated saline to neutrality dried over anhydrous sodium sulfate The solvent was removed Distillation under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 3 g LiAlH4 was added 100 ml anhydrous ethyl ether. While cooling with ice-bath and stirring intensely, 0.05 mol diethyl 2,2′-biphenyldicarboxylate was slowly added dropwise. The reaction mixture was heated refluxing for 5 hours, then cooled. Excess LiAlH4 was decomposed with water. The mixture was filtered, and the filtrate was extracted with ethyl ether. The extract was dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 2,2′-biphenyldimethanol as a white solid, the yield was 75%, and m.p. was 98-103° C. IR spectrum had a strong absorption peak at 3400 cm−1, and had no absorption peak at about 1700 cm−1. This demonstrated that the reduction reaction was carried out completely. While cooling with ice-bath The reaction mixture was heated refluxing for 5 hours cooled The mixture was filtered the filtrate was extracted with ethyl ether The extract was dried over anhydrous sodium sulfate The solvent was removed

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 0.1 mol 2,2′-biphenyl dicarboxylic acid anhydride were added 0.3 mol ethanol, 40 ml toluene, and 0.4 ml concentrated sulfuric acid with stirring. Then the reaction mixture was heated refluxing and the water produced was removed by using a water separator until the amount of the water separated reached theoretical value. Upon the reaction completion, the mixture was neutralized with saturated sodium carbonate solution and extracted with ethyl acetate. The upper layer was separated, washed with saturated saline to neutrality, and dried over anhydrous sodium sulfate. The solvent was removed. Distillation under reduced pressure gave diethyl 2,2′-biphenyldicarboxylate as a colorless liquid, and the yield was 90%. Then the reaction mixture was heated refluxing was removed separated extracted with ethyl acetate The upper layer was separated washed with saturated saline to neutrality dried over anhydrous sodium sulfate The solvent was removed Distillation under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 3 g LiAlH4 was added 100 ml anhydrous ethyl ether. While cooling with ice-bath and stirring intensely, 0.05 mol diethyl 2,2′-biphenyldicarboxylate was slowly added dropwise. The reaction mixture was heated refluxing for 5 hours, then cooled. Excess LiAlH4 was decomposed with water. The mixture was filtered, and the filtrate was extracted with ethyl ether. The extract was dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 2,2′-biphenyldimethanol as a white solid, the yield was 75%, and m.p. was 98-103° C. IR spectrum had a strong absorption peak at 3400 cm−1, and had no absorption peak at about 1700 cm−1. This demonstrated that the reduction reaction was carried out completely. While cooling with ice-bath The reaction mixture was heated refluxing for 5 hours cooled The mixture was filtered the filtrate was extracted with ethyl ether The extract was dried over anhydrous sodium sulfate The solvent was removed

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 0.1 mol 2,2′-biphenyl dicarboxylic acid anhydride were added 0.3 mol ethanol, 40 ml toluene, and 0.4 ml concentrated sulfuric acid with stirring. Then the reaction mixture was heated refluxing and the water produced was removed by using a water separator until the amount of the water separated reached theoretical value. Upon the reaction completion, the mixture was neutralized with saturated sodium carbonate solution and extracted with ethyl acetate. The upper layer was separated, washed with saturated saline to neutrality, and dried over anhydrous sodium sulfate. The solvent was removed. Distillation under reduced pressure gave diethyl 2,2′-biphenyldicarboxylate as a colorless liquid, and the yield was 90%. Then the reaction mixture was heated refluxing was removed separated extracted with ethyl acetate The upper layer was separated washed with saturated saline to neutrality dried over anhydrous sodium sulfate The solvent was removed Distillation under reduced pressure