Isobutanol → 1,1-Bis(2-methylpropoxy)cyclohexane

HRID 1609386Notes

Reaction equation

HRID 1609386 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:8]1[CH2:13][CH2:12]CCC=1.C[CH2:15][O:16]CC.C[O-].[Na+].[CH2:22](O)[CH:23]([CH3:25])[CH3:24]>>[CH2:22]([O:7][C:1]1([O:16][CH2:15][CH:13]([CH3:12])[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 4

HCID 6560IsobutanolHCID 7967CyclohexanoneHCID 10942334Sodium MethoxideHCID 18936963HCID 18936963, compound

Product 1

HCID 569964311,1-Bis(2-methylpropoxy)cyclohexane

Procedure

Since the sump analysis exhibited values of 79% CHIBK, 16% isobutanol, and 1% each of methyl isobutyl mixed ketal, cyclohexanone and cyclohexene ether (more than 90% conversion of cyclohexanone), the reaction mixture was neutralized with 1 g of sodium methylate, and the distillation was commenced. Under reduced pressure of initially 20 hPa and then further reduced to 5 hPa, isobutanol and the other side products were distilled off. At a boiling point of 98° C./5 hPa without reflux the cyclohexanone diisobutyl ketal was removed at the head of the column. The preliminary fraction which distilled off in advance was composed of 95 g (65% isobutanol, 17% CHIBK, cyclohexanone, cyclohexene ether and mixed ketals), together 0.21 mol CHIBK, cyclohexanone and derivatives thereof.

Workup

  1. distillationthe distillation
  2. distillationthe other side products were distilled off
  3. temperatureAt a boiling point of 98° C./5 hPa without reflux the cyclohexanone diisobutyl ketal
  4. customwas removed at the head of the column
  5. distillationThe preliminary fraction which distilled off in advance
  6. additionwas composed of 95 g (65% isobutanol, 17% CHIBK, cyclohexanone, cyclohexene ether and mixed ketals), together 0.21 mol CHIBK, cyclohexanone

Sources & evidence

ORD record
ord-650f270b843b4faeb808e03d389894d7
Source dataset
uspto-grants-1995_03
Patent number
US05399778

Reaction notes

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