3-(Carboxymethyl)-2-chlorobenzoic acid → 2-Chloro-3-(2-hydroxyethyl)benzaldehyde

HRID 1255249Notes

Reaction equation

HRID 1255249 reaction equation
[C:1]([CH2:4][C:5]1[C:6]([Cl:14])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])(O)=[O:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:14][C:6]1[C:5]([CH2:4][CH2:1][OH:2])=[CH:13][CH:12]=[CH:11][C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 1

HCID 579889673-(Carboxymethyl)-2-chlorobenzoic acid2×

Product 1

HCID 579889292-Chloro-3-(2-hydroxyethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Manganese (IV) dioxide (43.1 g) was added to a slight suspension of 2-(2-chloro-3-(hydroxymethyl)phenyl)ethanol [Aromatic Intermediate 11, step d] (18.5 g) in chloroform (500 mL), and the resulting suspension was heated at reflux for 2 h. The reaction mixture was cooled, filtered through Celite and the filter pad washed with DCM (3×300 mL). The combined washings and filtrate were evaporated and the residue purified by flash silica chromatography eluting with 3:1 to 1:1 isohexane:ethyl acetate gradient. The fractions containing product were combined and evaporated to give the titled compound as a white solid. Yield 12.00 g.

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux for 2 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through Celite
  5. washthe filter pad washed with DCM (3×300 mL)
  6. customThe combined washings and filtrate were evaporated
  7. customthe residue purified by flash silica chromatography
  8. washeluting with 3:1 to 1:1 isohexane
  9. additionThe fractions containing product
  10. customevaporated

Sources & evidence

ORD record
ord-e5cc821c6f6a4275a0a86d7103c1f25e
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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