Acetaldehyde → 3,3,5-Trimethylcyclohexanone

HRID 268185

Reaction equation

HRID 268185 reaction equation
N[C:2]1([O:11]O)[CH2:7][CH:6]([CH3:8])[CH2:5][C:4]([CH3:10])([CH3:9])[CH2:3]1.C(=O)C.[O-]O>>[CH3:8][CH:6]1[CH2:5][C:4]([CH3:10])([CH3:9])[CH2:3][C:2](=[O:11])[CH2:7]1

Participants

4

Reactant 3

HCID 177AcetaldehydeHCID 18500Perhydroxyl radicalHCID 215101831-Amino-3,3,5-trimethylcyclohexyl hydroperoxide

Product 1

HCID 133983,3,5-Trimethylcyclohexanone

Procedure

1-Amino-3,3,5-trimethylcyclohexyl hydroperoxide (17.3 g; 78% pure) was added with stirring to acetaldehyde (12 g.) in light petroleum (b.p. 40° - 60°C) 50 c.c.) with cooling to below 0°C. When the hydroperoxide had dissolved, the organic layer was separated, treated with solid magnesium sulphate and stored at 0°C overnight. The solution was then filtered, washed and distilled as in Example 1 and gave, in addition to dihydroisophorone, the same product (13.0 g.) as Example 1.

Workup

  1. temperature) with cooling to below 0°C
  2. customthe organic layer was separated
  3. additiontreated with solid magnesium sulphate
  4. filtrationThe solution was then filtered
  5. washwashed
  6. distillationdistilled as in Example 1

Sources & evidence

ORD record
ord-d90cc0dadaa946b7a39b97087ad71427
Source dataset
uspto-grants-1976_03
Patent number
US03947406

Linked notes

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