Isopropanol → 3,3-Diphenylpropyl methanesulfonate

HRID 1496692Notes

Reaction equation

HRID 1496692 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(O)(C)C>ClCCl>[CH3:24][S:25]([O:10][CH2:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 299083,3-DiphenylpropanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 222382923,3-Diphenylpropyl methanesulfonateYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

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).

Workup

  1. customwas conducted at 25° C
  2. customAfter the completion of reaction
  3. washthe reaction solution was washed with water thrice
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customevaporated
  6. customto remove the solvent
  7. customto produce an oily crude product
  8. filtrationThe resulting mixture was filtered by suction

Sources & evidence

ORD record
ord-fd7e67c3aa09438ea582ae6163b9a1d9
Source dataset
uspto-grants-2015_12
Patent number
US09198902B2

Reaction notes

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