Water → HCID 22999217, compound

HRID 1166765Notes

Reaction equation

HRID 1166765 reaction equation
[Br:1][CH2:2][CH2:3]Br.[CH:5](=[O:17])[C:6]1[CH:16]=[C:13]([O:14][CH3:15])[C:11]([OH:12])=[C:8]([O:9][CH3:10])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][CH2:2][CH2:3][O:12][C:11]1[C:13]([O:14][CH3:15])=[CH:16][C:6]([CH:5]=[O:17])=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 8655SyringaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 22999217HCID 22999217, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-Dibromoethane (47 mL, 0.55 moles) was added to a mixture of syringaldehyde (10 g, 55 mmoles) and potassium carbonate (38 g, 275 mmoles) in DMF (150 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 (3×300 mL). The combined organic phases were washed with saturated sodium chloride (500 mL), dried over MgSO4 and evaporated in vacuo to afford 3.44 g (22%) of 4-(2-bromoethoxy)-3,5-dimethoxybenzaldehyde.

Workup

  1. extractionextracted with ethyl acetate (3×300 mL)
  2. washThe combined organic phases were washed with saturated sodium chloride (500 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5f84915e75bc4ae585004627d22585b2
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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