Dimethylformamide → 2-Methoxymethyloxy-4,5,6-trimethoxybenzaldehyde

HRID 248556Notes

Reaction equation

HRID 248556 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1(O)[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH2:6]1.C([Li])CCC.CN([CH:26]=[O:27])C>CCOCC>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[C:6]=1[CH:26]=[O:27]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 677585271-Methoxymethyloxy-3,4,5-trimethoxyphenolHCID 178418339Butyllithium

Product 1

HCID 200957082-Methoxymethyloxy-4,5,6-trimethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

30.4 g of 1-methoxymethyloxy-3,4,5-trimethoxyphenol prepared in Referential Example 10 was dissolved in 250 ml of anhydrous ether, and 100 ml of n-butyllithium (1.6 M n-hexane solution) was dropwise added thereto at -20° C. After the completion of the dropwise addition, the mixture was stirred at room temperature for 2 hr, and 14.6 ml of DMF was added thereto. 100 ml of ice water was added thereto, and the mixture was extracted with ethyl acetate. The organic phase was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent; n-hexane ethyl acetate=6 : 4) to prepare 25.5 g of the product compound as a light yellow oleaginous substance.

Workup

  1. customat -20° C
  2. additionAfter the completion of the dropwise addition
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel column chromatography (eluent; n-hexane ethyl acetate=6 : 4)
  8. customto prepare 25.5 g of the product compound as a light yellow oleaginous substance

Sources & evidence

ORD record
ord-6239c4899b33416ab49267d3315a3347
Source dataset
uspto-grants-1993_05
Patent number
US05210239

Reaction notes

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