p-Toluenesulfonic acid → HCID 19973607, compound

HRID 2398090Notes

Reaction equation

HRID 2398090 reaction equation
C(O)CCO.C(C=C)=O.[C:10]1([CH3:20])[CH:15]=CC(S(O)(=O)=O)=C[CH:11]=1.[CH:21]([CH:23]1[O:28]CCC[O:24]1)=[CH2:22]>O>[CH:21]([CH:23]1[O:28][CH2:11][CH:10]([CH3:20])[CH2:15][O:24]1)=[CH2:22]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7847Acrolein3×HCID 104421,3-PropanediolHCID 800432-Vinyl-1,3-dioxane2×

Product 1

HCID 19973607HCID 19973607, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
26 °C

Procedure

For the sake of comparison, a mixture of 0.5 mole 1,3-propanediol and 0.55 mole acrolein were reacted at 50° C in the presence of 0.3 g. p-toluenesulfonic acid. Layers did not separate until the reaction mixture was cooled to 26° C. The mixture gave 18 g. of an aqueous layer which contained about 40% diol, 21% acrolein, 10% 2-vinyl-1,3-dioxane and 25% water. The acetal layer of 49 g. contained 63% 2-vinyl-1,3-dioxane, 23% acrolein, 8% diol and 5% water, conversion to acetal was about 60% which represents only a negligible increase over equilibrium conversion.

Workup

  1. customwere reacted at 50° C in the presence of 0.3 g
  2. customLayers did not separate until the reaction mixture
  3. customThe mixture gave 18 g
  4. temperaturea negligible increase over equilibrium conversion

Sources & evidence

ORD record
ord-1089ba5253cf43a1abaa83aa753ace14
Source dataset
uspto-grants-1977_05
Patent number
US04024159

Reaction notes

Loading…