Potassium Carbonate → (2,2-Diethoxyethyl)(3-methoxyphenyl)sulfane

HRID 354075Notes

Reaction equation

HRID 354075 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH:18]([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>CC(C)=O>[CH2:20]([O:19][CH:18]([O:22][CH2:23][CH3:24])[CH2:17][S:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 849893-Methoxybenzenethiol

Product 1

HCID 13642516(2,2-Diethoxyethyl)(3-methoxyphenyl)sulfaneYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-methoxybenzenethiol (15.0 mL, 120 mmol) and potassium carbonate (16.6 gm, 120 mmol) in 150 mL of acetone at room temperature was added dropwise 2-bromo-1,1-diethoxy-ethane (16.5 mL, 110 mmol). The reaction mixture was stirred at room temperature for 16 hours. The solids in the reaction mixture were removed by filtration and were washed well with acetone. The filtrate was concentrated. The residue was diluted with water and extracted several times with ether. The ether layers were combined and washed with 0.5 M KOH, water, brine, and were then dried over anhydrous sodium sulfate, filtered, and concentrated to yield 28.2 gm of the title compound.

Workup

  1. customThe solids in the reaction mixture were removed by filtration
  2. washwere washed well with acetone
  3. concentrationThe filtrate was concentrated
  4. additionThe residue was diluted with water
  5. extractionextracted several times with ether
  6. washwashed with 0.5 M KOH, water, brine
  7. dry with materialwere then dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f139167a7c694674bcb5877b01154f35
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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