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

HRID 325350Notes

Reaction equation

HRID 325350 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-27a0ab81073c481a8180f2e3d1ab0138
Source dataset
uspto-grants-1984_04
Patent number
US04440774

Reaction notes

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