Sodium Chloride → HCID 22999174, compound

HRID 1166759Notes

Reaction equation

HRID 1166759 reaction equation
[Br:1][CH2:2][CH2:3]Br.[CH3:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([CH3:15])[C:13]=1[OH:14])[CH:9]=[O:10].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>CN(C=O)C.O>[Br:1][CH2:2][CH2:3][O:14][C:13]1[C:6]([CH3:5])=[CH:7][C:8]([CH:9]=[O:10])=[CH:11][C:12]=1[CH3:15]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 752223,5-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 22999174HCID 22999174, compoundYield 106.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1,2-Dibromoethane (26 mL, 0.3 moles) was added to a mixture of 3,5-dimethyl-4-hydroxybenzaldehyde (4.57 g, 30 mmoles) and potassium carbonate (21 g, 150 mmoles) in DMF (90 ml) and the resulting mixture was stirred vigorously at room temperature for 16 hours. The mixture was poured into water (0.3 L), added saturated sodium chloride (200 mL) and extracted with ethyl acetate (2×200 mL). The combined organic phases were washed with saturated sodium chloride (300 mL), dried over MgSO4 and evaporated in vacuo to afford 8.2 g (95%) of 4-(2-bromoethoxy)-3,5-dimethylbenzaldehyde as an oil.

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. washThe combined organic phases were washed with saturated sodium chloride (300 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-91337634d4934f4297e6aba2c2554428
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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