Methyl iodide → 1-Chloro-4-[(4-methoxybutyl)sulfanyl]benzene

HRID 1703546Notes

Reaction equation

HRID 1703546 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[CH:6][CH:5]=1.[H][H].[CH3:18]I>C1(C)C=CC=CC=1>[CH3:18][O:15][CH2:14][CH2:13][CH2:12][CH2:11][S:10][C:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 272884-(P-chlorophenylthio)butanolHCID 178418361HCID 178418361, compound

Product 1

HCID 227621161-Chloro-4-[(4-methoxybutyl)sulfanyl]benzeneYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of 7.2 g of a 57% oil dispersion of sodium hydride and 125 ml of toluene was added a solution of 36.5 g of 4-(p-chlorophenylthio)butanol in 125 ml of toluene. The mixture was stirred and heated under reflux until the evolution of hydrogen ceased. It was then cooled and 25.6 g of methyl iodide was added with stirring. The resulting mixture was heated under reflux for 2 hours, cooled, washed with three portions of water saturated with sodium chloride, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was distilled at reduced pressure to give 17.1 g of product, b.p. 92°-100° at 0.05 mm, ND25 1.5524.

Workup

  1. temperatureheated
  2. temperatureIt was then cooled
  3. stirringwith stirring
  4. temperatureThe resulting mixture was heated
  5. temperatureunder reflux for 2 hours
  6. temperaturecooled
  7. washwashed with three portions of water saturated with sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated to dryness
  10. distillationThe residue was distilled at reduced pressure

Sources & evidence

ORD record
ord-f1c67a3080494134b9ee6603db8627aa
Source dataset
uspto-grants-1978_11
Patent number
US04124723

Reaction notes

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