2-Phenylethanol → Methanesulfonic acid, 2-phenylethyl ester

HRID 1773860Notes

Reaction equation

HRID 1773860 reaction equation
[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH2:8]([O:9][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 60542-PhenylethanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 146679Methanesulfonic acid, 2-phenylethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-phenylethanol (24.4 g, 0.2 mole) in CH2Cl2 (200 mL) is added NEt3 (30.7 mL, 0.22 mole). The reaction mixture is cooled to 0° C. and methanesulfonyl chloride (16.3 mL, 0.21 mole) is added dropwise. The reaction mixture is allowed to reach room temperature and is stirred at room temperature overnight. Solvent is removed under reduced pressure. Water is added and the aqueous phase is extracted three times with Et2O. The organic phase is washed with water, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure to give methanesulfonic acid phenethyl ester.

Workup

  1. customto reach room temperature
  2. customSolvent is removed under reduced pressure
  3. additionWater is added
  4. extractionthe aqueous phase is extracted three times with Et2O
  5. washThe organic phase is washed with water, brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-d6910f16b73e49cd9e87621c1a070bb6
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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