1-Butanol → 1,1-Dibutoxycyclohexane

HRID 482138

Reaction equation

HRID 482138 reaction equation
O.[C:2]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:9]([OH:13])[CH2:10][CH2:11][CH3:12]>C1(C)C=CC=CC=1>[CH2:7]([O:8][C:2]1([O:13][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 962WaterHCID 7967Cyclohexanone

Product 1

HCID 2437181,1-DibutoxycyclohexaneYield 187.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

In a 300-ml three-necked flask equipped with a water separator, 98 g (1 mole) of cyclohexanone, 148 g (2 moles) of n-butanol, 2.4 mg of stannous chloride dihydrate and 40 g of toluene were charged. The resulting mixture was heated at 125° C. under atmospheric pressure for 6 hours in a nitrogen atmosphere while removing the water formed from the reaction mixture by azeotropic distillation. When water was no longer distilled, the solvent (toluene) and unreacted starting materials were distilled off under reduced pressure. Distillation of the residue under reduced pressure gave 214.3 g of cyclohexanone dibutyl acetal [R1, R2 =a pentamethylene group and R3 =a n-butyl group] (boiling point: 102° C./3 mmHg) (yield: 94.0%).

Workup

  1. additionwere charged
  2. customwhile removing the water
  3. customformed from the reaction mixture by azeotropic distillation
  4. distillationWhen water was no longer distilled
  5. distillationwere distilled off under reduced pressure
  6. distillationDistillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-542f35a4804e41f38e9363201eecef33
Source dataset
uspto-grants-1998_08
Patent number
US05792876

Linked notes

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