Butanal → 1,1-Dibutoxybutane

HRID 1707807Notes

Reaction equation

HRID 1707807 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[C:6]1([CH3:16])[CH:11]=[CH:10]C(S(O)(=O)=O)=CC=1.[CH:17](=[O:21])[CH2:18][CH2:19][CH3:20].[OH-].[Na+]>O.C1CCCCC1>[CH2:1]([O:5][CH:17]([O:21][CH2:10][CH2:11][CH2:6][CH3:16])[CH2:18][CH2:19][CH3:20])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 261ButanalHCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 14798Sodium Hydroxide

Product 1

HCID 222101,1-Dibutoxybutane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8078CyclohexaneSolvent

Procedure

889.5 g of n-butanol, 1500 g of cyclohexane, and 5.7 g of p-toluenesulfonic acid are placed in a 4 liter three-necked flask fitted with a stirrer, dropping funnel, reflux condenser, and internal thermometer. 432.7 g of n-butyraldehyde is added with stirring over a period of 5 minutes. Owing to the acetal formation which starts spontaneously, the internal temperature rises to about 35° C. The mixture is allowed to react at 35° C. to 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 200 mbar and a bottom temperature up to 160° C.

Workup

  1. customfitted with a stirrer
  2. temperaturereflux condenser
  3. customrises to about 35° C
  4. customto react at 35° C. to 40° C. for 30 minutes
  5. customthe water phase is separated
  6. customTo remove the low-boiling components
  7. distillationdistillation at 200 mbar
  8. customup to 160° C.

Sources & evidence

ORD record
ord-521fc2617ab14474a362765b2174014f
Source dataset
uspto-grants-1994_10
Patent number
US05354911

Reaction notes

Loading…