Reaction #1583874

Reaction equation

3,3-diphenyl-1-propanol

triethylamine

isopropanol

MsCl

→

3,3-diphenylpropyl methanesulfonate

Yield 73.3%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherwas conducted at 25° C
2. 2
   OtherAfter the completion of reaction
3. 3
   Washthe reaction solution was washed with water thrice
4. 4
   DryingThe organic phase was dried over anhydrous sodium sulfate
5. 5
   Otherevaporated
6. 6
   Otherto remove the solvent
7. 7
   Otherto produce an oily crude product
8. 8
   FiltrationThe resulting mixture was filtered by suction

Procedure

3,3-diphenyl-1-propanol (1000 g, 4.7 mol) was dissolved in 3 L dichloromethane. To the mixture was added triethylamine (712 g, 7.05 mol). After stirring at 0° C. for half an hour, to the resulting mixture was slowly added MsCl (645 g, 5.64 mol) dropwisely. The reaction was conducted at 25° C. After the completion of reaction monitored by TLC, the reaction solution was washed with water thrice. The organic phase was dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce an oily crude product. To the crude product was added isopropanol. The resulting mixture was filtered by suction to produce 3,3-diphenylpropyl methanesulfonate as a solid (1000 g) in a yield of 73% (two steps together).

Source