4-Hydroxybenzaldehyde → 4-(3-Bromopropoxy)benzaldehyde

HRID 377640Notes

Reaction equation

HRID 377640 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][CH2:8][CH2:9][CH2:10]Br.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1>CC(C)=O>[Br:7][CH2:8][CH2:9][CH2:10][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 80011,3-DibromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 137157894-(3-Bromopropoxy)benzaldehydeYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (1.82 g, 13 mmol) and 1,3-dibromopropane (3.05 mL, 30 mmol) were added to a solution of 4-hydroxy-benzaldehyde (1.22 g, 10 mmol) in acetone (30 mL). The mixture was heated under reflux for 8.5 hrs. Then the reaction mixture was filtered and the solvent was removed by evaporation. The resulting residue was mixed with ether and then washed consecutively with 5% NaOH, water, and brine. After drying with MgSO4 and evaporation of the solvent, flash column chromatography (silica gel, hexane 100%>EtOAc:hexane=10:90>20:80) gave the desired compound as a pale yellow oil: Rf=0.71 (silica gel, EtOAc:hexane=35:65); yield 61%; 1H-NMR (300 MHz, CDCl3) δ9.86 (1H, s), 7.82-7.79 (2H, dd, J=6.9 and 1.8 Hz), 7.00-6.97 (2H, dd, J=7.1 and 1.6 Hz), 4.19-4.15 (2H, t, J=5.8 Hz), 3.61-3.56 (2H, t, 6.4 Hz), 2.37-2.28 (2H, qui, 6 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 8.5 hrs
  3. filtrationThen the reaction mixture was filtered
  4. customthe solvent was removed by evaporation
  5. additionThe resulting residue was mixed with ether
  6. washwashed consecutively with 5% NaOH, water, and brine
  7. dry with materialAfter drying with MgSO4 and evaporation of the solvent, flash column chromatography (silica gel, hexane 100%>EtOAc:hexane=10:90>20:80)

Sources & evidence

ORD record
ord-b22914580726476890575a581d84a4e2
Source dataset
uspto-grants-2000_02
Patent number
US06028088

Reaction notes

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