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

HRID 985726Notes

Reaction equation

HRID 985726 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][C:13]([Cl:15])=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:15][CH2:13][CH2:12][CH2:11][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 11430Potassium CarbonateHCID 84944Propanoyl chloride, 3-bromo-

Product 1

HCID 35514794-(3-Chloropropoxy)-benzaldehydeYield 75.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-hydroxybenzaldehyde (100 mmol, 12.2 g), 3-bromopropionyl chloride (101 mmol, 20 mL) and potasium carbonate (20.7 g, 150 mmol) in acetone (250 mL) was heated at reflux for overnight. The salt was filtered off. The solvent was evaporated. Reduced pressure distillation provided the title compound (15 g).

Workup

  1. temperatureat reflux for overnight
  2. filtrationThe salt was filtered off
  3. customThe solvent was evaporated
  4. distillationReduced pressure distillation

Sources & evidence

ORD record
ord-208e391071a845ec9c512e97d87f6b99
Source dataset
uspto-grants-2005_03
Patent number
US06872834B2

Reaction notes

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