Réaction #1583878

Équation de réaction

methanol

diisobutylaluminum hydride

methyl 2,2-diphenylacetate

sodium hydroxide

→

2,2-diphenyl ethanol

Rendement 92.4%

Solvants

dichloromethane

toluene

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter the completion of dropwise addition
2. 2
   AutreAfter the completion of reaction
3. 3
   Autreat −20° C
4. 4
   AutreAfter the completion of reaction
5. 5
   Extractionfor extraction
6. 6
   LavageThe organic phase was washed with water
7. 7
   Séchagedried over anhydrous sodium sulfate
8. 8
   Autreevaporated
9. 9
   Autreto remove the solvent

Mode opératoire

To a 500 mL three-opening flask was slowly added a solution of diisobutylaluminum hydride in toluene (282 mL, 1 mol/L) at −30° C. After stirring, to the resulting mixture was slowly added a solution of methyl 2,2-diphenylacetate (21 g, 92.8 mmol) in dichloromethane dropwisely. After the completion of dropwise addition, the reaction was conducted at 25° C. for 12 hours. After the completion of reaction monitored by TLC, to the resulting mixture was slowly added methanol (10 mL), dichloromethane (100 mL) and an aqueous sodium hydroxide solution (100 mL, 1 mol/L) at −20° C. After the completion of reaction, to the reaction solution was added dichloromethane for extraction. The organic phase was washed with water, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce 2,2-diphenyl ethanol (17 g) in a yield of 92.4%.

Source