Iodoethane → 1-(Ethylthio)-3-methoxybenzene

HRID 724282Notes

Reaction equation

HRID 724282 reaction equation
[OH-].[K+].[CH2:3](I)[CH3:4].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([SH:14])[CH:11]=[CH:12][CH:13]=1>C(O)C>[CH2:3]([S:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:7][CH3:6])[CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 849893-Methoxybenzenethiol

Product 1

HCID 6414391-(Ethylthio)-3-methoxybenzeneYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Solid potassium hydroxide (2.2 g, 39 mmol) and ethyl iodide (3.14 ml, 39 mmol) were added to a solution of 3-methoxybenzenethiol (5.0 g, 35 mmol) in ethanol (35 ml) (Caution—exotherm). The mixture was stirred for 72 h, then partitioned between water and ethyl acetate. The organic phase was dried over MgSO4 and the solvent removed under reduced pressure to give 1-(ethylsulfanyl)-3-methoxybenzene (5.9 g) as a yellow liquid.

Workup

  1. custompartitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a2550a87e30e43479fa85a84fc6eb2de
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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