HCID 68698382, compound → 3,5-Diethoxy-4-methoxybenzaldehyde

HRID 1990886Notes

Reaction equation

HRID 1990886 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:15][OH:16])[CH:7]=[C:8]([O:12][CH2:13][CH3:14])[C:9]=1[O:10][CH3:11])[CH3:2]>C1COCC1.O=[Mn]=O>[CH2:13]([O:12][C:8]1[CH:7]=[C:6]([CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:9]=1[O:10][CH3:11])[CH:15]=[O:16])[CH3:14]

Participants

4

Reactant 1

HCID 68698382HCID 68698382, compound

Product 1

HCID 587063513,5-Diethoxy-4-methoxybenzaldehydeYield 48%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3,5-diethoxy-4-methoxy-phenyl)-methanol (0.26 g, 1.15 mmol, 1.0 equiv) in THF (10 mL) was added activated MnO2 (1.0 g, 11.49 mmol, 10.0 equiv) and the reaction mixture stirred at rt for 4 h. Filtration through Hyflo Super Cel, concentration by evaporation under reduced pressure and purification with column chromatography on silica eluting with hexane/ethyl acetate (5:1) yielded 0.12 g (48%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.47 (t, J=7.0 Hz, 6H), 3.94 (s, 3H), 4.14 (q, J=7.0 Hz, 4H), 7.10 (s, 2H), 9.84 (s, 1H). MS (ISP): 225.1 [M+H]+.

Workup

  1. filtrationFiltration
  2. concentrationthrough Hyflo Super Cel, concentration
  3. customby evaporation
  4. customunder reduced pressure and purification with column chromatography on silica eluting with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-a8c4757608a04c99a51a56eabe92e75d
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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