Water → HCID 57304004, compound

HRID 439567Notes

Reaction equation

HRID 439567 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8](Br)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][O:14][CH3:15])[CH2:2][CH2:3][CH3:4].C([Li])CCC.CN(C)[CH:24]=[O:25].O>O1CCCC1>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][O:14][CH3:15])[CH:24]=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 57306543HCID 57306543, compoundHCID 178418339Butyllithium

Product 1

HCID 57304004HCID 57304004, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-butoxy-4-(methoxymethyl) oxybromobenzene (910 mg, 2.97 mmol) in tetrahydrofuran (15 ml) chilled at -72° C. was dropwise added n-butyllithium (2.22 ml, 3.56 mmol, 1.6M hexane solution) under nitrogen atmosphere, and 20 minutes later dimethylformamide (0.28 ml, 3.62 mmol) was added to the mixture, which was stirred for 30 minutes at the same temperature. The reaction mixture was mixed with water, and the product was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. The residue was chromatographed on a column of silica gel to give 3-butoxy-4-(methoxymethyl) oxybenzaldehyde (556 mg, 84%).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-92ec831609354a3183a286718cf36cb2
Source dataset
uspto-grants-1996_05
Patent number
US05514711

Reaction notes

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