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

HRID 470975Notes

Reaction equation

HRID 470975 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.[OH:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][CH2:2][CH2:3][CH2:4][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

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

Product 1

HCID 137157894-(3-Bromopropoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,3-dibromopropane (20.0 g) was added to a stirred suspension of 4-hydroxybenzaldehyde (4.0 g) and potassium carbonate (7.0 g) in acetone (80 mL). After 16 h, the mixture was heated under reflux for a further 2 h, cooled, filtered to remove the inorganics, and the solution was evaporated in vacuo. Purification was by silica gel chromatography eluting with isohexane to remove the 1,3-dibromopropane and then dichloromethane:isohexane, 2:1 to collect the subtitled compound. Yield 3.45 g.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for a further 2 h
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove the inorganics
  6. customthe solution was evaporated in vacuo
  7. customPurification
  8. washeluting with isohexane
  9. customto remove the 1,3-dibromopropane
  10. customdichloromethane:isohexane, 2:1 to collect the subtitled compound

Sources & evidence

ORD record
ord-80a01af5c18e48bda6bb67c5829455f4
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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