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

HRID 1258943Notes

Reaction equation

HRID 1258943 reaction equation
[Br:1][CH2:2][CH2:3]Br.[OH:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[Br:1][CH2:2][CH2:3][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1

Participants

6

Reactant 3

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

Product 1

HCID 2627064-(2-Bromoethoxy)BenzaldehydeYield 44%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,2-dibromoethane (3.9 mL, 45 mmol), 4-hydroxybenzaldehyde (1.8 g, 15 mmol) and K2CO3 (10.4 g, 75 mmol) in acetone (40 mL) was heated to reflux for 18 hr. The mixture was cooled, diluted with ethyl acetate (200 mL) and washed with brine (200 mL). Then organic layer was dried (MgSO4), filtered and then concentrated. The resulting residue was subjected to flash chromatography (25% ethyl acetate/hexane) to provide 1.51 g (44%) of 4-(2-bromoethoxy)benzaldehyde.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hr
  3. temperatureThe mixture was cooled
  4. washwashed with brine (200 mL)
  5. dry with materialThen organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-85726534dce74d4887f09df81c13e79e
Source dataset
uspto-grants-2013_06
Patent number
US08466193B2

Reaction notes

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