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

HRID 458706Notes

Reaction equation

HRID 458706 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[Br:12][CH2:13][CH2:14]Br>C(O)C>[Br:12][CH2:13][CH2:14][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 78391,2-DibromoethaneHCID 14797Potassium Hydroxide

Product 1

HCID 2627064-(2-Bromoethoxy)BenzaldehydeYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of potassium hydroxide (3.70 g, 54.0 mmol) in ethanol (50 ml) is added 4-hydroxybenzaldehyde (6.00 g, 49.1 mmol) and 1,2-dibromoethane (46.15 g, 245.7 mmol). Then the mixture is heated to reflux for 8 hours. After cooled, the reaction mixture is evaporated under vacuum. The residue is dissolved in water and extracted with dichloromethane (3×50 ml). The organic phase is washed with water (3×50 ml), dried over MgSO4 and evaporated to give a crude product, which is crystallized from ethanol to give the title compound (4.60 g, 41%).

Workup

  1. temperatureThen the mixture is heated
  2. temperatureto reflux for 8 hours
  3. temperatureAfter cooled
  4. customthe reaction mixture is evaporated under vacuum
  5. dissolutionThe residue is dissolved in water
  6. extractionextracted with dichloromethane (3×50 ml)
  7. washThe organic phase is washed with water (3×50 ml)
  8. dry with materialdried over MgSO4
  9. customevaporated
  10. customto give a crude product, which
  11. customis crystallized from ethanol

Sources & evidence

ORD record
ord-081536bf505a4c359eb2f8162c9d53af
Source dataset
uspto-grants-2007_03
Patent number
US07192970B2

Reaction notes

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