Sodium Hydroxide → 1-Methoxy-3-(3-methylbut-2-enylsulphanyl)benzene

HRID 1699429Notes

Reaction equation

HRID 1699429 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].[CH3:12][C:13](=[CH:15][CH2:16]Br)[CH3:14]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH2:16][CH:15]=[C:13]([CH3:14])[CH3:12])[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 700922-Butene, 1-bromo-3-methyl-HCID 849893-Methoxybenzenethiol

Product 1

HCID 225925921-Methoxy-3-(3-methylbut-2-enylsulphanyl)benzeneYield 90.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

50.45 g (360.0 mmol) of 3-methoxythiophenol, 360 ml of acetone and 14.40 g (360.0 mmol) of sodium hydroxide pellets are introduced into a one liter round-bottomed flask under a nitrogen atmosphere and the mixture is heated at reflux for three hours. A solution composed of 53.65 g (360.0 mmol) of 2-methyl-4-bromo-2-butene and of 60 ml of acetone is added dropwise. Reflux is maintained for sixteen hours and the reaction mixture is evaporated to dryness. Water is added, extraction is carried out with ethyl acetate, the organic phase is washed with water and then using a saturated sodium chloride solution, dried over magnesium sulphate and filtered, and the solvents are evaporated. The residue obtained is distilled under reduced pressure (5×10−2 bar/113° C.) to produce 67.81 g (90%) of the expected compound in the form of a pale-yellow oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for three hours
  3. additionis added dropwise
  4. temperatureReflux
  5. temperatureis maintained for sixteen hours
  6. customthe reaction mixture is evaporated to dryness
  7. additionWater is added
  8. extractionextraction
  9. washthe organic phase is washed with water
  10. dry with materialdried over magnesium sulphate
  11. filtrationfiltered
  12. customthe solvents are evaporated
  13. customThe residue obtained
  14. distillationis distilled under reduced pressure (5×10−2 bar/113° C.)

Sources & evidence

ORD record
ord-b99352c3b8664da5b3ac36205e32a450
Source dataset
uspto-grants-2002_02
Patent number
US06346546B1

Reaction notes

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