Butanal → Butanal

HRID 1576885Notes

Reaction equation

HRID 1576885 reaction equation
[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].N[C:7]1([O:16]O)[CH2:12][CH:11]([CH3:13])[CH2:10][C:9]([CH3:15])([CH3:14])[CH2:8]1.S([O-])([O-])(=O)=O.[Mg+2]>S(=O)(=O)(O)O>[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:13][CH:11]1[CH2:10][C:9]([CH3:15])([CH3:14])[CH2:8][C:7](=[O:16])[CH2:12]1

Participants

6

Reactant 3

HCID 261ButanalHCID 24083Sulfuric acid magnesium salt (1:1)HCID 215101831-Amino-3,3,5-trimethylcyclohexyl hydroperoxide

Product 2

HCID 261ButanalHCID 133983,3,5-Trimethylcyclohexanone

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Butyraldehyde (14.4 g.) was mixed with petrol (b.p. 40° - 60°) (50 c.c.) and to the stirred solution at below 0°C was added 1-amino-3,3,5-trimethylcyclohexyl hydroperoxide (17.3 g.; 89% pure). The peroxide dissolved within a few minutes. To the solution were added magnesium sulphate and concentrated sulphuric acid (6 drops) and the mixture stored at 0°C overnight. The solution was filtered, the filtrate washed with water, dried and distilled to give unreacted butyraldehyde, dihydroisophorone and a product (11.1 g.), b.p. 85° - 110°C/1.0 mm. with a peroxide equivalent of 231, and a perchloric equivalent of 233. The elemental analysis gave C, 68.6%; H, 11.05%; N, 6.6%. The product was identified as: ##SPC55##

Workup

  1. filtrationThe solution was filtered
  2. washthe filtrate washed with water
  3. customdried
  4. distillationdistilled

Sources & evidence

ORD record
ord-c26072bd30e74211b0b9cb1a8ff53526
Source dataset
uspto-grants-1976_09
Patent number
US03983142

Reaction notes

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