Methanol → 3-(Dimethoxymethyl)pentane

HRID 1707809Notes

Reaction equation

HRID 1707809 reaction equation
[CH3:1][OH:2].[C:3]1([CH3:13])[CH:8]=[CH:7]C(S(O)(=O)=O)=[CH:5][CH:4]=1.C(C(CC)[CH:17]=[O:18])C.[OH-].[Na+]>O.C1CCCCC1>[CH3:1][O:2][CH:13]([O:18][CH3:17])[CH:3]([CH2:8][CH3:7])[CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 73592-EthylbutyraldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 156562873-(Dimethoxymethyl)pentane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8078CyclohexaneSolvent

Procedure

417.3 g of methanol, 1625 g of cyclohexane, and 6.2 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. 651.3 g of 2-ethylbutyraldehyde is added with stirring over a 5 minute period. Owing to the acetal formation which starts spontaneously, the internal temperature rises to about 32° 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 200 mbar and a bottom temperature up to 105° C.

Workup

  1. customfitted with a stirrer
  2. temperaturereflux condenser
  3. customrises to about 32° 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 200 mbar
  8. customup to 105° C.

Sources & evidence

ORD record
ord-9bf53c8009e0428dbc496886da44702c
Source dataset
uspto-grants-1994_10
Patent number
US05354911

Reaction notes

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