反应详情

Lithium aluminum hydride (12.60 grams, 0.332 mol) and THF (175 ml) were placed in a dry 500 ml three-necked round-bottomed flask fitted with a condenser, addition funnel, nitrogen inlet, and magnetic stirrer. The mixture was cooled with an ice bath and diphenic acid (40.00 grams, 0.165 mol) in THF (100 ml) was added dropwise to the stirring mixture. After the addition was complete, the flask was removed from the ice bath and allowed to warm to room temperature. The reaction mixture was heated at reflux for 2 hours, then stirred overnight at room temperature. After cooling the mixture with an ice bath, water (12.6 ml) was added dropwise, followed by the successive dropwise addition of 15% aqueous sodium hydroxide (12.6 ml) and water (38 ml). The resulting yellow mixture was warmed to room temperature, and the solids were separated by vacuum filtration. The filtrate was placed on a rotary evaporator to remove the solvent. The remaining brownish-yellow solid was recrystallized from toluene-hexane to give 28.60 grams (81% yield) of light brown solid product, melting point 105° to 108° C.

1. customfitted with a condenser, addition funnel, nitrogen inlet, and magnetic stirrer
2. temperatureThe mixture was cooled with an ice bath
3. additionAfter the addition
4. customthe flask was removed from the ice bath
5. temperatureThe reaction mixture was heated
6. temperatureat reflux for 2 hours
7. temperatureAfter cooling the mixture with an ice bath
8. additionwater (12.6 ml) was added dropwise
9. additionfollowed by the successive dropwise addition of 15% aqueous sodium hydroxide (12.6 ml) and water (38 ml)
10. temperatureThe resulting yellow mixture was warmed to room temperature
11. customthe solids were separated by vacuum filtration
12. customThe filtrate was placed on a rotary evaporator
13. customto remove the solvent
14. customThe remaining brownish-yellow solid was recrystallized from toluene-hexane
15. customto give 28.60 grams (81% yield) of light brown solid product, melting point 105° to 108° C.