Butanal → HCID 178450112, compound

HRID 1086760Notes

Reaction equation

HRID 1086760 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[N:9][NH:10][CH:11]=1.[CH:13](=O)[CH2:14][CH2:15][CH3:16].[CH:18]1([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C1CCCCC1>[CH:18]1([O:24][CH:13]([C:1]2([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]2[C:7]2[N:8]=[N:9][NH:10][CH:11]=2)[CH2:14][CH2:15][CH3:16])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 261ButanalHCID 6101p-Toluenesulfonic acidHCID 7966CyclohexanolHCID 178424185HCID 178424185, compound

Product 1

HCID 178450112HCID 178450112, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8078CyclohexaneSolvent

Procedure

A mixture of 133 parts tolyltriazole, 79.3 parts n-butyraldehyde, 100.1 parts cyclohexanol and 1.3 parts paratoluene sulphonic acid is heated in 600 parts cyclohexane with simultaneous azeotropic removal of the water formed during the reaction. The reaction is complete after 2 hours. Upon cooling to ambient temperature, the reaction mixture is washed with dilute sodium carbonate solution, then with water and finally dried over anhydrous magnesium sulphate. The dried reaction mixture is filtered and evaporated under reduced pressure and then stripped under vacuum (100° C./4 Pa) to yield 262.9 parts (91.5 %) of 1-(1-cyclohexyloxybutyl) tolyltriazole as a yellow oil. The product is distilled at 175° C./8 Pa to yield a pale yellow oil.

Workup

  1. customformed during the reaction
  2. washthe reaction mixture is washed with dilute sodium carbonate solution
  3. dry with materialwith water and finally dried over anhydrous magnesium sulphate
  4. customThe dried reaction mixture
  5. filtrationis filtered
  6. customevaporated under reduced pressure
  7. customstripped under vacuum (100° C./4 Pa)

Sources & evidence

ORD record
ord-e8da9f9c78c54ccc9da7f9ce487e6f5e
Source dataset
uspto-grants-1991_07
Patent number
US05032300

Reaction notes

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