Sulfuric Acid → 1,3-Dimethoxy-2-(methylthio)benzene

HRID 660624Notes

Reaction equation

HRID 660624 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.CN(CCN(C)C)C.[Li]CCCC.[CH3:24][S:25]SC.S(=O)(=O)(O)O>CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[S:25][CH3:24]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 90251,3-DimethoxybenzeneHCID 12232Dimethyl DisulfideHCID 178418339Butyllithium

Product 1

HCID 6035511,3-Dimethoxy-2-(methylthio)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,3-dimethoxybenzene (1.94 mL, 15 mmol) and TMEDA (2.35 mL, 15.75 mmol) in ether (40 mL) a under nitrogen atmosphere at 0° C. is added dropwise n-BuLi (9.84 mL, 1.6M in hexane, 15.75 mmol). The mixture is stirred at 0° C. for 30 min then dimethyl disulfide (1.33 mL, 15 mmol) is added and stirring is continued at RT for 30 min. The mixture is poured into dilute sulfuric acid and the ether layer is separated. The aqueous is extracted with ether. The ether solutions are combined and washed with water and brine then dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound as a white solid.

Workup

  1. stirringstirring
  2. waitis continued at RT for 30 min
  3. customthe ether layer is separated
  4. extractionThe aqueous is extracted with ether
  5. washwashed with water and brine
  6. dry with materialthen dried over sodium sulfate
  7. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-272f449b10664f6290ccc7e0297ad6b0
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…