Iodoethane → Benzene, 1-(ethylthio)-4-methyl-

HRID 1777811Notes

Reaction equation

HRID 1777811 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.I[CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:10]([S:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH3:11]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 78114-MethylbenzenethiolHCID 11430Potassium Carbonate

Product 1

HCID 136431Benzene, 1-(ethylthio)-4-methyl-Yield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-methylbenzenethiol (100 g, 0.8 mol) in acetone (1 L) was added iodoethane (190 g, 1.2 mol) and potassium carbonate (220 g, 1.6 mol). The mixture was stirred at 60° C. overnight. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford crude ethyl(p-tolyl)sulfane (120 g, 99%) as a yellow solid, which was used for the next step without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-831f55a70d6344c1aa8f9b3915ac774a
Source dataset
uspto-grants-2016_02
Patent number
US09266886B2

Reaction notes

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