Sodium Hydroxide → 2-Ethyl-6-methoxybenzaldehyde

HRID 254468

Reaction equation

HRID 254468 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O: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]([O:9][CH3:10])[C:4]=1[CH:11]=[O:20])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178436445HCID 178436445, compound

Product 1

HCID 118589792-Ethyl-6-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.0 g (E)-[1-(2-ethyl-6-methoxy-phenyl)-methylidene]-(1-isopropyl-2-methyl-propyl)-amine in 1 ml THF and 0.19 ml 4N HCl was heated to reflux for 1 hour then cooled to ambient temperature and poured onto a 1N aqueous 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: 0.50 g 2-ethyl-6-methoxy-benzaldehyde as colourless oil: MS (EI): 261.2 (M+.), 218.2 ((M-((CH3)2CH))+., 100%).

Workup

  1. temperatureto reflux for 1 hour
  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-cc2e1f364d6f465b9ca5dfe30ccda2b8
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Linked notes

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