Propanal → Propane, 1,1-diethoxy-

HRID 1707806Notes

Reaction equation

HRID 1707806 reaction equation
[CH2:1]([OH:3])[CH3:2].[C:4]1([CH3:14])[CH:9]=CC(S(O)(=O)=O)=CC=1.[CH:15](=[O:18])[CH2:16]C.[OH-].[Na+]>O.C1CCCCC1>[CH2:1]([O:3][CH:9]([O:18][CH2:15][CH3:16])[CH2:4][CH3:14])[CH3:2]

Participants

7

Reactant 4

HCID 527PropanalHCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 14798Sodium Hydroxide

Product 1

HCID 20858Propane, 1,1-diethoxy-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8078CyclohexaneSolvent

Procedure

To 553.2 g of ethanol, 900 g of cyclohexane, and 5.7 g of p-toluenesulfonic acid placed in a 4 liter three-necked flask fitted with a stirrer, dropping funnel, reflux condenser, and internal thermometer, 348.6 g of propionaldehyde are added with stirring in the course of 5 minutes. Owing to the acetal formation, which starts spontaneously, the internal temperature rises to about 40° C. The mixture is allowed to react at 40° C. for 30 minutes, a pH of 7.0 is then established in the reaction mixture, which is composed of a lower water phase and an upper organic phase, by addition of sodium hydroxide solution (20% aqueous solution) and the water phase is separated. To remove the low-boiling components, the organic phase is subjected to initial distillation at 1013 mbar and a bottom temperature up to 121° C.

Workup

  1. customfitted with a stirrer
  2. temperaturereflux condenser
  3. customrises to about 40° C
  4. customto react at 40° C. for 30 minutes
  5. customthe water phase is separated
  6. customTo remove the low-boiling components
  7. distillationdistillation at 1013 mbar
  8. customup to 121° C.

Sources & evidence

ORD record
ord-e77d9281aa2c4db5aa0637884a472a6f
Source dataset
uspto-grants-1994_10
Patent number
US05354911

Reaction notes

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