Dimethylformamide → 2,4-Bis-methoxymethoxy-6-methoxymethyl-benzaldehyde

HRID 1798080Notes

Reaction equation

HRID 1798080 reaction equation
Br[C:2]1[C:7]([CH2:8][O:9][CH3:10])=[CH:6][C:5]([O:11][CH2:12][O:13][CH3:14])=[CH:4][C:3]=1[O:15][CH2:16][O:17][CH3:18].[Li]CCCC.CN([CH:27]=[O:28])C>CCOCC>[CH3:18][O:17][CH2:16][O:15][C:3]1[CH:4]=[C:5]([O:11][CH2:12][O:13][CH3:14])[CH:6]=[C:7]([CH2:8][O:9][CH3:10])[C:2]=1[CH:27]=[O:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 582927852-Bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzeneHCID 178418339Butyllithium

Product 1

HCID 582925712,4-Bis-methoxymethoxy-6-methoxymethyl-benzaldehydeYield 81.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene (10.5 g, 32.8 mmol) in Et2O (100 mL) was treated with n-BuLi (28.7 mL, 71.9 mmol) at −78° C. for 1 h. Then, DMF (27.7 mL, 359 mmol) was added to the reaction and the resulting mixture was warmed to room temperature for 3 h. The reaction was quenched with water and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=2:1) affording the title compound (7.21 g). 1H NMR (300 MHz, CD3OD) δ 10.49 (s, 1H), 7.46 (s, 1H), 6.45 (s, 1H), 5.27 (s, 2H), 5.24 (s, 2H), 4.83 (s, 2H), 3.51 (s, 3H). 3.50 (s, 3H), 3.49 (s, 3H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-2706003124ed465f98405ba942f32c0d
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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