1-Propanol → HCID 12731072, compound

HRID 1707808Notes

Reaction equation

HRID 1707808 reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].[CH2:5]1[CH2:10]CCC[CH2:6]1.[C:11]1([CH3:21])[CH:16]=[CH:15]C(S(O)(=O)=O)=C[CH:12]=1.[OH-:22].[Na+]>O>[CH2:1]([O:4][CH:15]([O:22][CH2:6][CH2:5][CH3:10])[CH2:16][CH:11]([CH3:12])[CH3:21])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 10311-PropanolHCID 6101p-Toluenesulfonic acidHCID 8078CyclohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 12731072HCID 12731072, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 841.4 g of n-propanol, 1750 g of cyclohexane, and 6.7 g of p-toluenesulfonic acid placed in a 4 liter three-necked flask fitted with a stirrer, dropping funnel, reflux condenser, and internal thermometer, 602.7 g of 3-methylbutyrladehyde 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 100° C.

Workup

  1. customfitted with a stirrer
  2. temperaturereflux condenser
  3. additioninternal thermometer, 602.7 g of 3-methylbutyrladehyde is added
  4. customrises to about 35° C
  5. customto react at 35° C. to 40° C. for 30 minutes
  6. customthe water phase is separated
  7. customTo remove the low-boiling components
  8. distillationdistillation at 200 mbar
  9. customup to 100° C.

Sources & evidence

ORD record
ord-8fa3db1f66b14b7ebce45ad9dfdf5e9c
Source dataset
uspto-grants-1994_10
Patent number
US05354911

Reaction notes

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