1-Butanol → 1,1-Dibutoxycyclohexane

HRID 482143

Reaction equation

HRID 482143 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]([OH:12])[CH2:9][CH2:10][CH3:11].S([O-])([O-])(=O)=O.[Mg+2]>[Bi](Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH2:6]([O:7][C:1]1([O:12][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:1][CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 2631-ButanolHCID 7967CyclohexanoneHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 2437181,1-DibutoxycyclohexaneYield 182.2%

Reagents, catalysts & solvents 2

HCID 24591Bismuth trichlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

In a 300-ml three-necked flask, 98 g of cyclohexanone, 148 g of n-butanol, 50 g of anhydrous magnesium sulfate, 2 mg of bismuth chloride and 80 g of toluene were charged. The resulting mixture was stirred at 10° C. under atmospheric pressure for 10 hours in a nitrogen atmosphere. After magnesium sulfate was removed from the reaction mixture, the solvent (toluene) and unreacted starting materials were distilled off under reduced pressure. Distillation of the residue under reduced pressure gave 207.7 g of cyclohexanone dibutyl acetal (yield: 89.4%).

Workup

  1. customAfter magnesium sulfate was removed from the reaction mixture
  2. distillationwere distilled off under reduced pressure
  3. distillationDistillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-b875a7393a85409cb8f86ed45dbcfed7
Source dataset
uspto-grants-1998_08
Patent number
US05792876

Linked notes

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