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

HRID 1689415Notes

Reaction equation

HRID 1689415 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-4b96bf61c16d4c659ffce056338ae80a
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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