1-Butanol → 1,1-Dibutoxycyclohexane

HRID 482141

Reaction equation

HRID 482141 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]>O.O.O.O.O.O.[Cl-].[Ce+3].[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

5

Reactant 2

HCID 2631-ButanolHCID 7967Cyclohexanone

Product 1

HCID 2437181,1-DibutoxycyclohexaneYield 185.8%

Reagents, catalysts & solvents 2

HCID 22347666cerium(III) chloride hexahydrateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

In a 300-ml three-necked flask, 98 g (1 mole) of cyclohexanone, 148 g (2 moles) of n-butanol, 50 g of molecular sieve 4A, 2 mg of cerium chloride hexahydrate and 40 g of toluene were charged. The resulting mixture was stirred at 25° C. under atmospheric pressure for 12 hours in a nitrogen atmosphere. After the removal of the molecular sieve 4A, the solvent (toluene) and unreacted starting materials were distilled off under reduced pressure. Distillation of the residue under reduced pressure gave 212.2 g of cyclohexanone dibutyl acetal (yield: 93.1%).

Workup

  1. customAfter the removal of the molecular sieve 4A
  2. distillationwere distilled off under reduced pressure
  3. distillationDistillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-dae1db1790a9481699e48cfae4a326c1
Source dataset
uspto-grants-1998_08
Patent number
US05792876

Linked notes

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