Water → 1-Methyl-4-[4-(methylsulfanyl)phenoxy]-2-(propylsulfanyl)benzene

HRID 372459Notes

Reaction equation

HRID 372459 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[S:9][CH2:10][CH2:11][CH3:12].[OH-].[K+].Br[CH2:16][S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C(=O)C>[CH3:16][S:17][C:18]1[CH:23]=[CH:22][C:21]([O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([S:9][CH2:10][CH2:11][CH3:12])[CH:4]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 1501913HCID 1501913, compoundHCID 144045044-Methyl-3-(propylsulfanyl)phenol

Product 1

HCID 203277381-Methyl-4-[4-(methylsulfanyl)phenoxy]-2-(propylsulfanyl)benzene

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-Methyl-3-(n-propylthio)phenol (4.0 g, 0.02 mole) and 85.5 % potassium hydroxide (1.4 g, 0.02 mole) were dissolved in N,N-dimethylacetamide (40 ml) above 90° C. 4-Bromomethylthiobenzene (4.0 g, 0.02 mole) and Cu powder (0.5 g, 0.008 mole) were added to this solution below 90° C and the mixture was stirred at 120° - 160° C for 14 hr. After cooling, the reaction mixture was poured into water (100 ml) and extracted twice with benzene. The combined organic layers were washed with 5 % sodium hydroxide solution, 5 % hydrochloric acid solution, and water, then dried over sodium sulfate. The solvent was removed, and the residue was distilled under reduced pressure. The yield of 4-methyl-3-n-propylthiophenyl 4-methylthiophenyl ether was 4.1 g (61.5 %), colorless oil, bp 188° - 190° C/2 mmHg. Anal. Found: C, 67.12; H, 6.59. Calcd. for C17H20OS2 : C, 67.06; H, 6.62 %

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with benzene
  3. washThe combined organic layers were washed with 5 % sodium hydroxide solution, 5 % hydrochloric acid solution, and water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-115dad9d874248fc975338b82261d68b
Source dataset
uspto-grants-1978_05
Patent number
US04091109

Reaction notes

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