2-Chloroethyl methyl ether → HCID 554732, compound

HRID 1172022Notes

Reaction equation

HRID 1172022 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][S:5]([CH2:8][CH:9]([O:12][CH3:13])[O:10][CH3:11])(=O)=O.COCCCl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][S:5][CH2:8][CH:9]([O:10][CH3:11])[O:12][CH3:13]

Participants

5

Reactant 2

HCID 123162-Chloroethyl methyl etherHCID 1281589784373-91-1

Product 1

HCID 554732HCID 554732, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

In Example 13, involving synthesis of dimethoxyethyl sulfone (DMES), 50 ml 2-chloroethyl methyl ether, 70 g Na2S.9H2O, 17.6 g tetrabutylammonium bromide and 50 ml H2O were mixed into a three-neck flask equipped with magnetic stirrer and reflux condenser, and heated at 70° C. with vigorous stirring. The reaction was continued for overnight. The organic layer was separated and dissolved in chloroform, washed with distilled water several times to remove the ammonium salt and dried over anhydrous sodium sulfate. Solvent was removed using a rotary evaporator, and dimethoxyethyl sulfide was obtained with a yield of 63%. The sulfide was oxidized with H2O2 and acetic acid, as described in Example 1, to obtain the corresponding sulfone, dimethoxyethylsulfone (DMES).

Workup

  1. additionwere mixed into a three-neck flask
  2. customequipped with magnetic stirrer
  3. temperaturereflux condenser
  4. customThe organic layer was separated
  5. dissolutiondissolved in chloroform
  6. washwashed with distilled water several times
  7. customto remove the ammonium salt
  8. dry with materialdried over anhydrous sodium sulfate
  9. customSolvent was removed
  10. customa rotary evaporator

Sources & evidence

ORD record
ord-797d131c3a4f47b5a6e84a9e67f5edad
Source dataset
uspto-grants-2010_11
Patent number
US07833666B2

Reaction notes

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