2-(2-Chloro-3-(hydroxymethyl)phenyl)ethanol → 2-Chloro-3-(2-hydroxyethyl)benzaldehyde

HRID 471185Notes

Reaction equation

HRID 471185 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][OH:12]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[C:3]([CH2:10][CH2:11][OH:12])=[CH:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 1

HCID 579892482-(2-Chloro-3-(hydroxymethyl)phenyl)ethanol

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese (IV) dioxide (1.599 g) was added to a solution of 2-(2-chloro-3-(hydroxymethyl)phenyl)ethanol (example 80, step c) (0.342 g) in DCM (20 mL), and the resulting suspension was stirred at room temperature overnight. The mixture was then concentrated onto silica and purified by flash chromatography on silica eluted with 25% ethyl acetate in isohexane to afford the subtitled compound as a white crystalline solid. Yield 0.223 g.

Workup

  1. concentrationThe mixture was then concentrated onto silica
  2. custompurified by flash chromatography on silica
  3. washeluted with 25% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-025684fe684d4dc29f0e5f9c4b359b8e
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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