Triethylamine → 2,2-Diphenylethyl methanesulfonate

HRID 1496697

Reaction equation

HRID 1496697 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([O:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 74662beta-Phenylphenethyl alcohol

Product 1

HCID 117478202,2-Diphenylethyl methanesulfonateYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 500 mL three-opening flask, 2,2-diphenyl ethanol (17 g, 86 mmol) was dissolved in 170 mL dichloromethane. To the flask was added triethylamine (13.03 g, 129 mmol). The resulting mixture was stirred at 0° C. for half an hour. To the resulting mixture was slowly added MsCl (11.92 g, 104 mmol) 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 2,2-diphenylethyl methanesulfonate (23 g) in a yield of 96.78%.

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

Sources & evidence

ORD record
ord-461d3dd456204aa295305cd46e6fee34
Source dataset
uspto-grants-2015_12
Patent number
US09198902B2

Linked notes

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