p-Toluenesulfonic acid → HCID 53932472, compound

HRID 2170254Notes

Reaction equation

HRID 2170254 reaction equation
[CH3:1][CH:2](/[CH:8]=[CH:9]/[CH:10]=[C:11]([CH3:18])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH:3](OC)[O:4]C.C1COCC1.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>O>[CH3:1][CH:2]([CH:8]=[CH:9][CH:10]=[C:11]([CH3:18])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH:3]=[O:4]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 86674857HCID 86674857, compound

Product 1

HCID 53932472HCID 53932472, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 250 mL four-neck reaction flask protected from atmospheric moisture by nitrogen gas throughout the course of the reaction a mixture of 12.6 g of (E)-2,6,10-trimethyl-1,1-dimethoxy-3,5,9-undecatriene (0.05 mol) of formula (2A), 100 mL THF and 1.2 g of PTSA was added. After stirred until homogeneous, 22 g of water was added, and additional 24 h of stirring at 20˜25° C. was needed until the reaction completed according to GC. Then a solution of 2 g of NaHCO3 and 20 mL water was added for neutralization. After removal of THF by vacuum distillation, 100 mL of cyclohexane was added and then stratification. The organic layer was washed with 30 mL water, dried over anhydrous magnesium sulfate and subsequently filtered. Removal of the volatile organic solvents by evaporation at reduced pressure afforded 10.5 g of crude 2,6,10-trimethyl-3,5,9-undecatriene-1-aldehyde of formula (12).

Workup

  1. customTo a 250 mL four-neck reaction flask protected from atmospheric moisture by nitrogen gas throughout the course of the reaction
  2. additionwas added
  3. additionwas added
  4. customAfter removal of THF
  5. distillationby vacuum distillation, 100 mL of cyclohexane
  6. additionwas added
  7. washThe organic layer was washed with 30 mL water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationsubsequently filtered
  10. customRemoval of the volatile organic solvents
  11. customby evaporation at reduced pressure

Sources & evidence

ORD record
ord-04f034aa6fd64f13823b498823ff14d9
Source dataset
uspto-grants-2015_06
Patent number
US09051254B2

Reaction notes

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