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

HRID 33694Notes

Reaction equation

HRID 33694 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][CH2:13][Cl:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:14][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 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 35514794-(3-Chloropropoxy)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 4-hydroxybenzaldehyde (40 g), 1-bromo-3-chloropropane (63 mL), and potassium carbonate (136 g) in acetone (920 mL) was heated to reflux for 16 h. The resulting mixture was filtered, and the filtrate was evaporated. Distillation of the residue (0.5 mm Hg, 220° C.) gave the title compound as a pale yellow oil that crystallized on standing (46 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. filtrationThe resulting mixture was filtered
  4. customthe filtrate was evaporated
  5. distillationDistillation of the residue (0.5 mm Hg, 220° C.)

Sources & evidence

ORD record
ord-be361634a2bb4c15ac30b6b9117c6f1f
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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