Methanesulfonyl chloride → 2-Phenethyloxy-ethanol mesylate

HRID 1905964Notes

Reaction equation

HRID 1905964 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[CH3:13][S:14]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 132089292-(2-Phenylethoxy)ethanol

Product 1

HCID 132089412-Phenethyloxy-ethanol mesylateYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 2-(2-phenylethoxy)ethanol obtained according to the preceding paragraph was dissolved in 100 ml of pyridine. The solution was treated with 4.48 g of methanesulfonyl chloride and the mixture was stirred at room temperature for 0.5 hour. The solvent was removed by evaporation and the residue was partitioned between ethyl acetate and 2N hydrochloric acid. The organic phase was washed with water, dried over sodium sulfate, filtered and evaporated to give 8.1 g (85%) of 2-(2-phenylethoxy)ethyl methanesulfonate in the form of an oil which was homogeneous according to chromatography.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between ethyl acetate and 2N hydrochloric acid
  3. washThe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0da48d32649a4fbfa744d0d50ed173d4
Source dataset
uspto-grants-1987_03
Patent number
US04649160

Reaction notes

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