p-Toluenesulfonic acid → 3,3-Diethoxy-1-propene

HRID 991946Notes

Reaction equation

HRID 991946 reaction equation
[CH:1]([CH:3]=C)=O.C(O[CH:8]([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:13]([O:12][CH:8]([O:9][CH2:10][CH3:11])[CH:1]=[CH2:3])[CH3:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7847AcroleinHCID 31214Ethyl orthoformate

Product 1

HCID 624773,3-Diethoxy-1-propeneYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

After 10 ml of acrolein commercially available from Aldrich, Co. is dissolved in 50 ml of anhydroust ethanol, 19 ml of triethylorthoformate and p-toluene sulfonic acid are added to the solution, and the resulting mixture is allowed to reflux under a nitrogen atmosphere for 5 hours. After that, the resulting solution is cooled to a temperature of 5° C., extracted with diethyl ether, washed with 5% sodium bicarbonate (NaHCO3) aqueous solution, dried with anhydrous magnesium sulfate (MgSO4), and then evaporated under a reduced pressure to remove ethanol. Next, the material is fractionally distilled, thereby giving 8.4 g of 3,3-diethoxy-1-propene.

Workup

  1. temperatureto reflux under a nitrogen atmosphere for 5 hours
  2. extractionextracted with diethyl ether
  3. washwashed with 5% sodium bicarbonate (NaHCO3) aqueous solution
  4. dry with materialdried with anhydrous magnesium sulfate (MgSO4)
  5. customevaporated under a reduced pressure
  6. customto remove ethanol
  7. distillationNext, the material is fractionally distilled

Sources & evidence

ORD record
ord-8aad16a364bc48d687d70dc90074c42b
Source dataset
uspto-grants-2002_10
Patent number
US06465671B1

Reaction notes

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