Sodium Hydroxide → 2,6-Diethylbenzaldehyde

HRID 254463Notes

Reaction equation

HRID 254463 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1/[CH:11]=N/C(C(C)C)C(C)C)[CH3:2].[OH-:20].[Na+]>C1COCC1.Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[CH:11]=[O:20])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178436223HCID 178436223, compound

Product 1

HCID 131847782,6-Diethylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15.6 g (E)-[1-(2,6-diethyl-phenyl)-methylidene]-(1-isopropyl-2-methyl-propyl)-amine in 60 ml THF and 120 ml 4N HCl was heated to reflux for 2 hours then cooled to ambient temperature and poured onto a 1N NaOH solution. The aqueous phase was extracted with ethyl acetate, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash-chromatography on silica gel with a heptane/ethyl acetate gradient as eluent: 8.35 g 2,6-diethyl-benzaldehyde as light yellow oil: MS (EI): 162.1 (M+., 100%).

Workup

  1. temperatureto reflux for 2 hours
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe combined extracts washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash-chromatography on silica gel with a heptane/ethyl acetate gradient as eluent

Sources & evidence

ORD record
ord-d8f62fa020e1439b88cd4da06fe3d071
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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