Hydrochloric Acid → 2,6-Dichloro-4-hydroxybenzaldehyde

HRID 235930Notes

Reaction equation

HRID 235930 reaction equation
[OH-].[Ca+2].[OH-].[C:4](=O)([O-])[O-:5].[Na+].[Na+].[Cl:10][C:11]1[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([Cl:17])[CH:16]=1.Cl>O.C(Cl)(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([Cl:17])[C:16]=1[CH:4]=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 115713,5-DichlorophenolHCID 6093208Calcium Hydroxide

Product 1

HCID 5283822,6-Dichloro-4-hydroxybenzaldehydeYield 4.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a stirred suspension of calcium hydroxide (61 gm), sodium carbonate (69.7 gm), and 3,5 dichlorophenol (20.97 gm) in water (436 ml) at 74° is added chloroform (45.3 gm) over 90 minutes. The solution is refluxed for 31/2 hours. After the slow addition of concentrated hydrochloric acid (170 ml), the acidic solution is steam distilled the aqueous residue is cooled and the solid which separates is filtered. Recrystallization from toluene gives 1.1 gm of 2,6-dichloro-4-hydroxybenzaldehyde.

Workup

  1. temperatureThe solution is refluxed for 31/2 hours
  2. distillationdistilled the aqueous residue
  3. temperatureis cooled
  4. filtrationthe solid which separates is filtered
  5. customRecrystallization from toluene

Sources & evidence

ORD record
ord-f021b5cd402148ce9b4a8e91b8238cca
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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