Water → HCID 17753308, compound

HRID 1166766Notes

Reaction equation

HRID 1166766 reaction equation
[Br:1][CH2:2][CH2:3]Br.[OH:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:9]=[O:10].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][CH2:2][CH2:3][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 17753308HCID 17753308, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-Dibromoethane (56 mL, 0.66 moles) was added to a mixture of 3-hydroxy-4-methoxybenzaldehyde (10 g, 66 mmoles) and potassium carbonate (45 g, 328 mmoles) in DMF (170 ml) and the resulting mixture was stirred vigorously at room temperature for 16 hours. The mixture was poured into water (0.5 L) and extracted with ethyl acetate (3×200 mL). The combined organic phases were washed with saturated sodium chloride (500 mL), dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel (800 mL) eluting with a mixture of ethyl acetate and heptane (1:1) to afford 9.8 g (58%) of 3-(2-bromoethoxy)-4-methoxybenzaldehyde.

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. washThe combined organic phases were washed with saturated sodium chloride (500 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (800 mL)
  6. washeluting with a mixture of ethyl acetate and heptane (1:1)

Sources & evidence

ORD record
ord-7be153098f404f308fddd5c6ffc9a5a9
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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