Methyl iodide → HCID 12326071, compound

HRID 437992Notes

Reaction equation

HRID 437992 reaction equation
[CH:1]1([CH3:11])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([SH:10])[CH2:2]1.CI.[O-][CH2:15]C.[Na+]>C(O)C>[CH3:15][S:10][CH:3]1[CH:4]([CH:7]([CH3:8])[CH3:9])[CH2:5][CH2:6][CH:1]([CH3:11])[CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 12687248HCID 12687248, compound

Product 1

HCID 12326071HCID 12326071, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Menthane-3-thiol (3.5 g., 20 mmole), methyl iodide (3.5 g., 25 mmole) and sodium ethoxide in ethanol (25 ml. of 0.8 M solution) were mixed together and stirred at room temperature for 21/2 hours. The ethanol was then removed and water was added to the residue, which was extracted with ether. The ether extracts were dried (MgSO4) and the solvent was removed. The residue was eluted with 40/60 petroleum ether down a silica column and the product was distilled to give p-menth-3-yl methyl sulphide b.p. 83°-5°/0.05 mm.

Workup

  1. customThe ethanol was then removed
  2. additionwater was added to the residue, which
  3. extractionwas extracted with ether
  4. dry with materialThe ether extracts were dried (MgSO4)
  5. customthe solvent was removed
  6. washThe residue was eluted with 40/60 petroleum ether down a silica column
  7. distillationthe product was distilled

Sources & evidence

ORD record
ord-aa52e884631b4341b7d916e2cd8110eb
Source dataset
uspto-grants-1977_06
Patent number
US04032661

Reaction notes

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