Triethylamine → 1-(Methylsulfonyloxy)-2-[4-(methylsulfonyloxy)phenyl]ethane

HRID 1595491Notes

Reaction equation

HRID 1595491 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][OH:20])=[CH:16][CH:15]=1>ClCCl>[CH3:8][S:9]([O:20][CH2:19][CH2:18][C:17]1[CH:21]=[CH:22][C:14]([O:13][S:9]([CH3:8])(=[O:11])=[O:10])=[CH:15][CH:16]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10393TyrosolHCID 31297Methanesulfonyl chloride

Product 1

HCID 112201221-(Methylsulfonyloxy)-2-[4-(methylsulfonyloxy)phenyl]ethaneYield 88,080.203%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

27.3 g (0.27 mmole) triethylamine and a solution of 27.2 g (0.239 g mmole) methane sulfonyl chloride in dichloromethane were added to a solution of 15 g (0.108 mmole) p-hydroxyphenethyl alcohol in dichloromethane at 0° C. The reaction was allowed to reach room temperature, then stirred at room temperature and followed by TLC. The reaction mixture was filtered and the filtrate was washed with water. The solution was dried with sodium sulfate and then evaporated in vacuo to give 28 g (yield 88%) of 4-(methylsulfonyloxy)phenethyl methanesulfonate.

Workup

  1. customto reach room temperature
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate was washed with water
  4. dry with materialThe solution was dried with sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-322d526f34df4ce0abc55cfe86b2addc
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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