Reaction #1583873

Reaction equation

ethyl 3,3-diphenyl-1-propanate

diisobutylaluminum hydride

methanol

water

→

3,3-diphenyl-1-propanol

Yield 100.2%

Solvents

dichloromethane

toluene

Conditions

Workup

1. 1
   OtherTo a 30 L reaction kettle
2. 2
   workup.ADDITIONAfter the completion of dropwise addition
3. 3
   OtherAfter the completion of reaction
4. 4
   Otherto quench off
5. 5
   Otherthe reaction
6. 6
   Extractionextracted with dichloromethane
7. 7
   DryingThe organic phase was dried over anhydrous sodium sulfate
8. 8
   Otherevaporated
9. 9
   Otherto remove the solvent

Procedure

To a 30 L reaction kettle was slowly added a solution of diisobutylaluminum hydride in toluene (15 L, 1 mol/L) at −20° C. After stirring, to the resulting mixture was slowly added a solution of ethyl 3,3-diphenyl-1-propanate (1200 g, 4.7 mol) 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, the reaction solution was divided into three parts. 200 mL methanol and 1000 mL water were slowly added respectively at −20° C. to quench off the reaction. The reaction solutions were combined and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce an oily crude product of 3,3-diphenyl-1-propanol (1000 g), which was directly used in the next reaction.

Source