4-Hydroxybenzaldehyde → 4-(2-Bromoethoxy)Benzaldehyde

HRID 630381Notes

Reaction equation

HRID 630381 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:16][CH2:17][CH2:18]Br>C(O)C>[Br:16][CH2:17][CH2:18][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 2627064-(2-Bromoethoxy)BenzaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-hydroxybenzaldehyde (3 g, 0.024 mol) in ethanol (30 mL) was added potassium carbonate (6.6 g, 0.047 mol) and 1,2-dibromoethane (21 mL, 0.24 mol). The reaction mixture was stirred at 70° C. for 20 hours. The salts were filtrated and the filtrate was concentrated. The crude was dissolved in ethyl acetate and the organic layer was washed with water, sodium hydroxide 2N and brine, dried, and filtered. The organic solvent was removed under reduced pressure to give the title compound as a yellow-orange solid (88%), which was used in the next step without further purification.

Workup

  1. filtrationThe salts were filtrated
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe crude was dissolved in ethyl acetate
  4. washthe organic layer was washed with water, sodium hydroxide 2N and brine
  5. customdried
  6. filtrationfiltered
  7. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-408a1e948b684fe79401fdfd099407ca
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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