Toluene → 7,8-Dimethoxyoct-1-ene

HRID 1194299Notes

Reaction equation

HRID 1194299 reaction equation
[H-].[Na+].[CH2:3]([OH:12])[CH:4](O)[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10].[H][H].S([O:20][CH3:21])(OC)(=O)=O.[C:22]1(C)C=CC=CC=1>O.CO>[CH3:22][O:12][CH2:3][CH:4]([O:20][CH3:21])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10]

Participants

8

Reactant 5

HCID 1140Toluene2×HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 5652667-Octene-1,2-diolHCID 178418361HCID 178418361, compound

Product 1

HCID 30225797,8-Dimethoxyoct-1-eneYield 81.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

198 g (6.6 mol) of sodium hydride (80% strength) and 500 g of toluene are introduced into a flask, and the mixture is heated to the reflux temperature. 432 g (3 mol) of 7-octene-1,2-diol, dissolved in 1,500 g of toluene, are then added over 3 hours, and the mixture is stirred at the reflux temperature until hydrogen evolution is complete. 830 g (6.6 mol) of dimethyl sulphate are added over 4 hours, and the mixture is stirred for a further 2 hours. After addition of 50 ml of methanol, 1,500 g of water are added in order to dissolve the precipitate. The phases are separated and the organic phase is distilled. 420 g of 1,2-dimethoxyoct-7-ene having a boiling point of 80° C./10 mbar, corresponding to a yield of 81% of theory) are obtained.

Workup

  1. temperaturethe mixture is heated to the reflux temperature
  2. additionare then added over 3 hours
  3. additionare added in order
  4. dissolutionto dissolve the precipitate
  5. customThe phases are separated
  6. distillationthe organic phase is distilled

Sources & evidence

ORD record
ord-0c0e81db04a646ebb1824739c0ef821f
Source dataset
uspto-grants-1989_03
Patent number
US04814322

Reaction notes

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