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

HRID 456938Notes

Reaction equation

HRID 456938 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-2dc6edce85dc4f5a8477c7208418ea00
Source dataset
uspto-grants-2007_03
Patent number
US07186732B2

Reaction notes

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