Hydrochloric Acid → 1-Acetoxy-1-(3-chlorophenyl)-2-(2-methanesulfonyloxyethoxy)ethane

HRID 1198231Notes

Reaction equation

HRID 1198231 reaction equation
[C:1]([O:4][CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH2:6][O:7][CH2:8][CH2:9][OH:10])(=[O:3])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20].Cl>C(Cl)Cl.C(N(CC)CC)C>[C:1]([O:4][CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH2:6][O:7][CH2:8][CH2:9][O:10][S:19]([CH3:18])(=[O:21])=[O:20])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 537909691-Acetoxy-1-(3-chlorophenyl)-2-(2-hydroxyethoxy)ethane

Product 1

HCID 536841961-Acetoxy-1-(3-chlorophenyl)-2-(2-methanesulfonyloxyethoxy)ethane

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a mixture of 19.0 9 of 1-acetoxy-1-(3-chlorophenyl)-2-(2-hydroxyethoxy)ethane and 95.0 ml of methylene chloride containing 9.1 ml of methanesulfonyl chloride was dropwise added 16.4 ml of triethylamine with ice cooling over 1 hour. The resulting mixture was stirred for 10 minutes at the same temperature and further for 1 hour at room temperature. The reaction mixture was added to a mixture of 50.0 ml of methylene chloride and 50.0 ml of ice water. The resulting mixture was adjusted to pH 2.0 with 6N hydrochloric acid. The organic layer was separated, washed with water and dried over anhydrous magnesium sulfate The solvent was removed by distillation under reduced pressure to obtain 24.5 g of oily 1-acetoxy-1-(3-chlorophenyl)-2-(2-methanesulfonyloxyethoxy)ethane.

Workup

  1. customover 1 hour
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate The solvent
  5. customwas removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-b3cd9cb79c844b7ba37f91f645e42031
Source dataset
uspto-grants-1994_01
Patent number
US05280032

Reaction notes

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