Acetaldehyde → 3,3,5-Trimethylcyclohexanone

HRID 1576884Notes

Reaction equation

HRID 1576884 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 52 and gave, in addition to dihydroisophorone, the same product (13.0 g.) as Example 52.

Workup

  1. temperaturewith 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 52

Sources & evidence

ORD record
ord-5bdc90a4b32148f99966de88448a5caf
Source dataset
uspto-grants-1976_09
Patent number
US03983142

Reaction notes

Loading…