Butanal → n-Butanal dicrotyl acetal

HRID 482144

Reaction equation

HRID 482144 reaction equation
[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:6]([OH:10])[CH:7]=[CH:8][CH3:9]>C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Ti].C1(C)C=CC=CC=1>[CH2:1]([O:5][CH:6]([O:10][CH2:1][CH:2]=[CH:3][CH3:4])[CH2:7][CH2:8][CH3:9])[CH:2]=[CH:3][CH3:4]

Participants

5

Reactant 2

HCID 261ButanalHCID 200242-Buten-1-ol

Product 1

HCID 57271298n-Butanal dicrotyl acetalYield 190.7%

Reagents, catalysts & solvents 2

HCID 44629996tetrakis((Z)-4-hydroxypent-3-en-2-one);titaniumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

In a 300-ml three-necked flask, 72 g (1 mole) of n-butanal, 144 g of crotyl alcohol, 3 mg of titanium acetylacetonate, 80 g of molecular sieve 4A and 50 g of toluene were charged. The resulting mixture was stirred at 20° C. under atmospheric pressure for 12 hours in a nitrogen atmosphere. After the removal of the molecular sieve 4A from the reaction mixture, the solvent (toluene) and the unreacted starting materials were distilled off under reduced pressure. Distillation of the residue under reduced pressure gave 189.1 g of n-butanal dicrotyl acetal (boiling point: 116° C./25 mmHg) (yield: 95.5%).

Workup

  1. customAfter the removal of the molecular sieve 4A from the reaction mixture
  2. distillationthe solvent (toluene) and the unreacted starting materials were distilled off under reduced pressure
  3. distillationDistillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-1083e6383f0346da8a1eb6f0d2893a8a
Source dataset
uspto-grants-1998_08
Patent number
US05792876

Linked notes

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