3,5,5-Trimethyl-2-methylidenehexanal → Hexanal, 2,3,5,5-tetramethyl-

HRID 1721275Notes

Reaction equation

HRID 1721275 reaction equation
[CH2:1]=[C:2]([CH:5]([CH3:11])[CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:3]=[O:4]>[Pd]>[CH3:1][CH:2]([CH:5]([CH3:11])[CH2:6][C:7]([CH3:8])([CH3:10])[CH3:9])[CH:3]=[O:4]

Participants

3

Reactant 1

HCID 907733,5,5-Trimethyl-2-methylidenehexanal

Product 1

HCID 109323Hexanal, 2,3,5,5-tetramethyl-Yield 96%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

235 g of the propenal from Example 71 (1.48 moles) were hydrogenated on a Parr shaker with 2.5 g of 5% Pd on carbon. The resulting propanal, 231.8 g, was distilled to afford 221.7 g of purified product (96% yield). BP 59° C./5 mmHg; 1H-NMR (300 MHz), spectra consistent with assigned structures; 13C-NMR (75 MHz), spectra consistent with assigned structures; IR (Neat), 2980, 2700, 1730, 1480, 1370; MS (m/e), 141 (M+ -15), 123, 98, 83, 57 (Base);

Workup

  1. distillationThe resulting propanal, 231.8 g, was distilled

Sources & evidence

ORD record
ord-4d0ec717930d48f1b8b87f2c181e9584
Source dataset
uspto-grants-1996_04
Patent number
US05510326

Reaction notes

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