4-Chloro-2,6-bis(hydroxymethyl)phenol → 5-Chloro-2-hydroxyisophthalaldehyde

HRID 722303Notes

Reaction equation

HRID 722303 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[C:5]([OH:10])=[C:4]([CH2:11][OH:12])[CH:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]([OH:10])=[C:6]([CH:8]=[O:9])[CH:7]=1

Participants

4

Reactant 1

HCID 869144-Chloro-2,6-bis(hydroxymethyl)phenol

Product 1

HCID 1229125-Chloro-2-hydroxyisophthalaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred suspension of diol (Step 1) (33.0 g, 0.18 mole) in chloroform (1.5 L) in a 2 L round bottom flask was added manganese dioxide (139 g, 1.60 mole) and the resulting suspension heated to a gentle reflux for 10 hours. The reaction was allowed to cool to room temperature, was filtered through diatomaceous earth, concentrated in vacuo, presorbed on silica gel and purified by flash chromatography (hexane/ethyl acetate) yielding the as a mustard colored powder dialdehyde (22.42 g, 67%): mp 120.7–122.8° C. This solid was of suitable purity to use in the next step without further purification.

Workup

  1. temperaturethe resulting suspension heated to
  2. temperaturea gentle reflux for 10 hours
  3. filtrationwas filtered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography (hexane/ethyl acetate)
  6. customyielding the as a mustard
  7. customto use in the next step without further purification

Sources & evidence

ORD record
ord-8e3ce21ea54b453a8d371b9999a40048
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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