p-Toluenesulfonic acid → Decane, 1,1-dimethoxy-

HRID 347600Notes

Reaction equation

HRID 347600 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]C.[CH:12](OC)([O:15][CH3:16])[O:13][CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:14][O:13][CH:12]([O:15][CH3:16])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8175DecanalHCID 9005Trimethyl orthoformate

Product 1

HCID 24513Decane, 1,1-dimethoxy-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Decanal dimethyl acetal was prepared by reacting 796 g decanal with 763.5 g trimethyl orthoformate in the presence of 1.97 g p-toluene sulfonic acid dissolved in 6.07 g methanol at a temperature of 45° C. for a period of time of 0.33 hours. The resulting product was washed with an aqueous 2.5% sodium bicarbonate solution, and then with water; dried over anhydrous sodium sulfate; filtered through CELITE®/sodium sulfate and distilled at 92–98° C. at 4.36–4.97 mm Hg. Then, into a 2 liter reaction flask equipped with stirrer, thermometer, heating mantle, addition funnel, vacuum apparatus, and reflux condenser the following ingredients were added at 17° C.:

Workup

  1. washThe resulting product was washed with an aqueous 2.5% sodium bicarbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered through CELITE®/sodium sulfate
  4. distillationdistilled at 92–98° C. at 4.36–4.97 mm Hg
  5. customThen, into a 2 liter reaction flask
  6. customequipped with stirrer
  7. temperaturethermometer, heating
  8. additionmantle, addition funnel, vacuum apparatus
  9. temperaturereflux condenser the following ingredients
  10. additionwere added at 17° C.

Sources & evidence

ORD record
ord-c72a47b35ad748efa42bf047ba95a494
Source dataset
uspto-grants-2007_02
Patent number
US07175871B2

Reaction notes

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