Methyl iodide → 1,1-Dimethoxy-7-methylthio-3,7-dimethyloctane

HRID 1605131Notes

Reaction equation

HRID 1605131 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][CH:5]([CH3:13])[CH2:6][CH2:7][CH2:8][C:9]([SH:12])([CH3:11])[CH3:10].[CH3:16][O-].[Na+].CI>CO>[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][CH:5]([CH3:13])[CH2:6][CH2:7][CH2:8][C:9]([S:12][CH3:16])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 215493991,1-Dimethoxy-7-mercapto-3,7-dimethyloctane

Product 1

HCID 215493561,1-Dimethoxy-7-methylthio-3,7-dimethyloctane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 10 g. of 1,1-dimethoxy-7-mercapto-3,7-dimethyloctane, one equiv. of sodium methoxide and 100 ml. of methanol is added 1.5 equivalents of methyl iodide. The mixture is stirred for 2 hours at room temperature and then refluxed for 2 hours. After cooling to room temperature, solvent is removed by evaporation and the residue taken up in ether. The ether solution is washed with water, dried and evaporated under reduced pressure to give 1,1-dimethoxy-7-methylthio-3,7-dimethyloctane which can be purified by chromatography or distillation.

Workup

  1. additionTo a mixture of 10 g
  2. temperaturerefluxed for 2 hours
  3. temperatureAfter cooling to room temperature
  4. customsolvent is removed by evaporation
  5. washThe ether solution is washed with water
  6. customdried
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-eaeb01dc512c48c198438fad53d8582f
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

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