Methyl iodide → 4-(Allyloxy)-2-methoxy-1-(methylsulfanyl)benzene

HRID 724269Notes

Reaction equation

HRID 724269 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([SH:12])=[C:9](O)[CH:10]=1)[CH:2]=[CH2:3].[C:13](=[O:16])([O-])[O-].[K+].[K+].[CH3:19]I>CC(C)=O>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([S:12][CH3:19])=[C:9]([O:16][CH3:13])[CH:10]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 218771835-(Allyloxy)-2-sulfanylphenol

Product 1

HCID 218771484-(Allyloxy)-2-methoxy-1-(methylsulfanyl)benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-(Allyloxy)-2-sulfanylphenol (37.84 g, 0.21 mol) and potassium carbonate (43 g, 0.31 mol) in acetone (450 ml) was cooled to 5° C. and treated with methyl iodide (32.32 ml, 0.52 mol) dropwise and stirred for 1 h at RT. After removal of the solvent in vacuo, the residue was partioned between diethyl ether (300 ml) and water (400 ml). The aqueous phase was separated and extracted with further diethyl ether (2×150 ml) and the combined organics were dried over MgSO4 and evaporated to a clear oil (26 g, 0.12 mol).

Workup

  1. customAfter removal of the solvent in vacuo
  2. customThe aqueous phase was separated
  3. extractionextracted with further diethyl ether (2×150 ml)
  4. dry with materialthe combined organics were dried over MgSO4

Sources & evidence

ORD record
ord-4a589f2b4250443392094a9983cb5293
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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