Water → HCID 22999301, compound

HRID 1166764Notes

Reaction equation

HRID 1166764 reaction equation
[Br:1][CH2:2][CH2:3]Br.[OH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:16]=[O:17])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][CH2:2][CH2:3][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:16]=[O:17])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 3442904-Hydroxy-1-naphthaldehyde

Product 1

HCID 22999301HCID 22999301, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-Dibromoethane (30 mL, 0.35 moles) was added to a mixture of 4-hydroxy-1-naphthaldehyde (6 g, 35 mmoles) and potassium carbonate (24 g, 175 mmoles) in DMF (110 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 (300 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 8.5 g (88%) of 4-(2-bromoethoxy)-1-naphthaldehyde as a solid. M.p.: 83-84° C.

Workup

  1. extractionextracted with ethyl acetate (3×300 mL)
  2. washThe combined organic phases were washed with saturated sodium chloride (300 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-671f5e7be21f456c984f516f452b7123
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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