Reaction #1583878

Reaction equation

methanol

diisobutylaluminum hydride

methyl 2,2-diphenylacetate

sodium hydroxide

→

2,2-diphenyl ethanol

Yield 92.4%

Solvents

dichloromethane

toluene

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONAfter the completion of dropwise addition
2. 2
   OtherAfter the completion of reaction
3. 3
   Otherat −20° C
4. 4
   OtherAfter the completion of reaction
5. 5
   Extractionfor extraction
6. 6
   WashThe organic phase was washed with water
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   Otherevaporated
9. 9
   Otherto remove the solvent

Procedure

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